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
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)
- form
- Solid
- 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)
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)
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..…
N-Bromosuccinimide Price
- Product number
- M1824990
- Product name
- Metoclopramide
- Purity
- European Pharmacopoeia (EP) Reference Standard
- Packaging
- m1824990
- Price
- $220
- Updated
- 2024/03/01
- Product number
- 32473
- Product name
- Metoclopramide
- Purity
- VETRANAL
- Packaging
- 100mg
- Price
- $140
- Updated
- 2024/03/01
- Product number
- M338698
- Product name
- Metoclopramide
- Packaging
- 1g
- Price
- $65
- Updated
- 2021/12/16
- Product number
- H780
- Product name
- Metoclopramide
- Packaging
- 100mg
- Price
- $72
- Updated
- 2021/12/16
- Product number
- H780
- Product name
- Metoclopramide
- Packaging
- 1g
- Price
- $144
- Updated
- 2021/12/16
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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View Lastest Price from 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide manufacturers
- Product
- Metoclopramide 364-62-5
- Price
- US $0.00/g
- Min. Order
- 1g
- Purity
- More Than 99%
- Supply Ability
- 100kg/Month
- Release date
- 2024-10-11
- Product
- Metoclopramide 364-62-5
- Price
- US $0.00-0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 99%min
- Supply Ability
- 1000kg
- Release date
- 2021-09-14
- Product
- metoclopramide 364-62-5
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 0.98
- Supply Ability
- 1000
- Release date
- 2024-07-19