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ChemicalBook > CAS DataBase List > 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide

Uses
Product Name
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
CAS No.
364-62-5
Chemical Name
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
Synonyms
Metoclopramide;DEL;Metaclopramide;Primperan;Metochlopramide;C07868;Parmid;Plasil;del1267;DEL 1267
CBNumber
CB4506227
Molecular Formula
C14H22ClN3O2
Formula Weight
299.8
MOL File
364-62-5.mol
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4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Property

Melting point:
146-148°C
Boiling point:
418.7±45.0 °C(Predicted)
Density 
1.2432 (rough estimate)
refractive index 
1.5200 (estimate)
storage temp. 
2-8°C
solubility 
Practically insoluble in water, sparingly soluble or slightly soluble in ethanol (96 per cent), slightly soluble in methylene chloride
pka
pKa 0.42± 0.03;9.71± 0.02(H2O)(Approximate)
color 
White to Off-White
BRN 
1884366
CAS DataBase Reference
364-62-5(CAS DataBase Reference)
NIST Chemistry Reference
Benzamide, 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxy-(364-62-5)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-64
Safety Statements 
36/37
WGK Germany 
3
HS Code 
2924.29.7790
Hazardous Substances Data
364-62-5(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M1824990
Product name
Metoclopramide
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
m1824990
Price
$220
Updated
2024/03/01
Sigma-Aldrich
Product number
32473
Product name
Metoclopramide
Purity
VETRANAL
Packaging
100mg
Price
$140
Updated
2024/03/01
TRC
Product number
M338698
Product name
Metoclopramide
Packaging
1g
Price
$65
Updated
2021/12/16
AK Scientific
Product number
H780
Product name
Metoclopramide
Packaging
100mg
Price
$72
Updated
2021/12/16
AK Scientific
Product number
H780
Product name
Metoclopramide
Packaging
1g
Price
$144
Updated
2021/12/16
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4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Chemical Properties,Usage,Production

Uses

Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.

Chemical Properties

White or almost white, fine powder.

Originator

Primperan,Delagrange,France,1964

Uses

Metoclopramide is a treatment of choice of post-operative nausea and vomiting (PONV) prophylaxis.

Uses

antidiabetic

Definition

ChEBI: A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.

Manufacturing Process

The N-(diethylaminoethyl)-2-methoxy-4-aminobenzamide used as the starting material may be prepared from o-toluidine. The o-toluidine is initially nitrated with nitric acid to produce 4-nitro-o-toluidine. The 4-nitro-o-toluidine is then converted to 2-hydroxy-4-nitrotoluene by heating with nitrous acid. By reacting the resulting 2-hydroxy-4-nitrotoluene with dimethyl sulfate, 2- methoxy-4-nitrotoluene is formed. The 2-methoxy-4-nitrotoluene is oxidized with potassium permanganate to produce 2-methoxy-4-nitrobenzoic acid. The latter substituted benzoic acid is treated with thionyl chloride to form 2- methoxy-4-nitrobenzoyl chloride. A methyl ethyl ketone solution of the 2- methoxy-4-nitrobenzoyl chloride is added over a period of about 1? hours to a methyl ethyl ketone solution containing an equal molecular quantity of N,Ndiethylethylene diamine while stirring and maintaining the temperature between 0°C and 5°C. The N-(diethylaminoethyl)-2-methoxy-4- nitrobenzamide hydrochloride formed precipitates. It is filtered, washed twice with methyl ethyl ketone, dissolved in alcohol, and reduced catalytically in an absolute isopropyl alcohol solution to form N-(diethylaminoethyl)-2-methoxy- 4-aminobenzamide. The base is obtained by precipitating with sodium hydroxide.
80 g (0.3mol) of N-(2-diethylaminoethyl)-2-methoxy-4-aminobenzamide are dissolved in small portions in 150 cc of acetic acid. The mixture is cooled and 45 g (0.45 mol) of acetic anhydride are added, and the solution obtained is heated for two hours on a water bath. After cooling, the solution is decanted into a round-bottomed flask with a stirrer, a thermometer and a tube for introducing the chlorine. It is stirred and the current of chlorine is passed through, the temperature being maintained between 20°C and 25°C. The stirring is continued for one hour after the completion of the absorption of the chlorine.
The mixture obtained is poured into 2 liters of water and the base is precipitated with 30% soda. The precipitated base is extracted with 400 cc of methylene chloride. After evaporation of the solvent, the N-(2- diethylaminoethyl)-2-methoxy-4-acetamino-5-chlorobenzamide formed crystallizes. The melting point is 86°C to 87°C and the yield is 95%.
To obtain the corresponding amino derivative, 109 g of base are heated under agitation in a round-bottomed flask with 300 cc of 35-36% concentrated hydrochloric acid and 600 cc of water. It is heated on a water bath until dissolution is complete, then maintained at boiling point for 90 minutes, cooled, diluted with 1 liter of water, and neutralized with about 350 cc of 30% soda. The N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide formed crystallizes, is centrifuged and washed in water. Its melting point is 122°C and the yield is 74%.
To obtain the corresponding dihydrochloride, the base is dissolved in absolute alcohol (3 volumes) and to that solution is added 5 N alcoholic hydrochloric acid. The dihydrochloride precipitates, is centrifuged and washed with alcohol. It is a solid white material, having a melting point of 134°C to 135°C.

brand name

Maxolon (King); Reglan (Baxter Healthcare); Reglan (Robins); Reglan (Schwarz Pharma).

Therapeutic Function

Antiemetic

General Description

Metoclopramide is typically employed as an antiemetic drug or a gastrointestinal prokinetic drug in adults and children.

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Preparation Products And Raw materials

Raw materials

Preparation Products

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4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Suppliers

Jinan Chenghui Shuangda biological Co., LTD
Tel
0531-58897003 15550412551
Fax
0531-58897003
Email
market@jnchsd.com
Country
China
ProdList
208
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62
Shanghai Boyle Chemical Co., Ltd.
Tel
021-50182298 021-50180596
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2210
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44751
Advantage
61
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
zhangsn@titansci.com
Country
China
ProdList
14113
Advantage
59
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070 13913916777;
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
17840
Advantage
64
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696;
Email
info@hanhongsci.com
Country
China
ProdList
42982
Advantage
64
XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-0712-2580635 15527768850
Email
1791901229@qq.com
Country
China
ProdList
8850
Advantage
52
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View Lastest Price from 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide manufacturers

PNP Biotech Co. Ltd
Product
Metoclopramide 364-62-5
Price
US $0.00/kg
Min. Order
25kg
Purity
98%
Supply Ability
Inquiry
Release date
2022-10-19
shandong perfect biotechnology co.ltd
Product
metoclopramide 364-62-5
Price
US $0.00/g
Min. Order
1g
Purity
98% HPLC
Supply Ability
1ks
Release date
2023-08-03
Shaanxi Dideu Medichem Co. Ltd
Product
MetoclopraMide 364-62-5
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-06

364-62-5, 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamideRelated Search:


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