Basic information Safety Supplier Related

clorexolone

Basic information Safety Supplier Related

clorexolone Basic information

Product Name:
clorexolone
Synonyms:
  • 12833 RP
  • 6-Chloro-2-cyclohexyl-2,3-dihydro-3-oxo-1H-isoindole-5-sulfonamide
  • Flonatril
  • M&B 8430
  • Nefrolan
  • 6-chloro-2-cyclohexyl-3-keto-isoindoline-5-sulfonamide
  • 6-chloro-2-cyclohexyl-3-oxo-1H-isoindole-5-sulfonamide
  • Chlorexolone
CAS:
2127-01-7
MF:
C14H17ClN2O3S
MW:
328.818
EINECS:
2183426
Mol File:
2127-01-7.mol
More
Less

clorexolone Chemical Properties

Melting point:
266-268°
storage temp. 
Refrigerator
solubility 
DMSO (Slightly, Heated), Methanol (Very Slightly, Heated)
form 
Solid
color 
White to Off-White
More
Less

clorexolone Usage And Synthesis

Originator

Speciatensol,Specia,France,1966

Uses

Chlorexolone is a sulfonamide based antibiotic.

Uses

Chlorexolone is a low-ceiling sulfonamide diuretic.

Definition

ChEBI: Clorexolone is an organic molecular entity.

Manufacturing Process

4-Chlorophthalimide (263 g) was reacted in amyl alcohol (2.6 l) with cyclohexylamine (143.5 g, 1 mol) at reflux temperature for 16 hours to give N-cyclohexyl-4-chlorophthalimide (250 g, 66%) as a solid, MP 134°C to 136°C.
N-Cyclohexyl-1-chlorophthalimide (250 g) was dissolved in glacial acetic acid (2.5 l), concentrated hydrochloric acid (555 ml) and tin (278 g) were added and the suspension was heated on a steam bath for 16 hours. The cooled solution was filtered and concentrated to dryness in vacuo to give a white solid. This solid was dissolved in water and the precipitated oil extracted with chloroform. The chloroform solution was dried and concentrated in vacuo to give a solid which, after recrystallization, yielded 5-chloro-2- cyclohexylisoindolin-1-one (43%), MP 140°C to 142°C.
5-Chloro-2-cyclohexylisoindolin-1-one (102.9 g) was dissolved in concentrated sulfuric acid (665 ml); potassium nitrate (723 g) in concentrated sulfuric acid (166 ml) was added at 0 °C. The reaction mixture was allowed to warm to room temperature and stirred at 25°C for 12 hours. The reaction mixture was poured onto ice to give a cream solid which, after recrystallization from benzene, gave 5-chloro-2-cyclohexyl-6-nitroisoindolin-1-one (46.7 g, 44%) as a white solid, MP 164°C to 168°C.
5-Chloro-2-cyclohexyl-6-nitroisoindolin-1-one (93.9 g) was reduced in concentrated hydrochloric acid (1,970 ml) with stannous chloride (376 g). The reaction temperature rose to 70°C. The resulting solution was cooled in ice and filtered. The product was washed well with water, filtered and dried to give 6-amino-5-chloro-2-cyclohexylisoindolin-1-one (74.1 g, 87.6%) which, after recrystallization from benzene, had a MP of 216°C to 218°C.
6-Amino-5-chloro-2-cyclohexylisoindolin-1-one (42.5 g) was dissolved in concentrated hydrochloric acid (425 ml) and the solution diazotized by the addition of sodium nitrite (21.25 g) in water (125 ml). The resulting diazonium salt solution was added to a solution of liquid sulfur dioxide (93 ml) in glacial acetic acid (243 ml) containing cuprous chloride (2.25 g). A yellow solid was precipitated; this was filtered off, washed, dried and recrystallized from benzene to give 5-chloro-2-cyclohexylisoindolin-1-one-6-sulfonyl chloride (45 g, 80%) as a cream solid, MP 171°C to 174°C.
This sulfonyl chloride (23.7 g) was reacted with liquid ammonia (237 ml) to give 5-chloro-2-cyclohexyl-6-sulfamoylisoindolin-1-one (14.2 g, 53%). MP 259°C to 261°C.

Therapeutic Function

Diuretic

clorexoloneSupplier

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Email
jkinfo@jkchemical.com
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Email
sales@chemreagents.com
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Email
info@yuhaochemical.com
Capot Chemical Co.,Ltd.
Tel
+86-(0)57185586718 +86-13336195806
Email
sales@capot.com