Water → N'-(4-chlorocyclohexyl)-urea

HRID 1580324Notes

Reaction equation

HRID 1580324 reaction equation
C(NCCC1C=CC(S([NH:16][C:17]([NH:19][CH:20]2[CH2:25][CH2:24][CH:23]([Cl:26])[CH2:22][CH2:21]2)=[O:18])(=O)=O)=CC=1)(=O)C.[OH-].[Na+].O.COC1C=CC(Cl)=CC=1C(Cl)=O>CC(C)=O>[Cl:26][CH:23]1[CH2:22][CH2:21][CH:20]([NH:19][C:17](=[O:18])[NH2:16])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 21566308N-[4-(beta-acetoamido-ethyl)-benzenesulfonyl]-N'-(4-chlorocyclohexyl)-urea

Product 1

HCID 86732946N'-(4-chlorocyclohexyl)-urea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7.8 g of N-[4-(β-acetoamido-ethyl)-benzenesulfonyl]-N'-(4-chlorocyclohexyl)-urea (melting point 151° -153°C) are heated under reflux for 2 hours with 1.6 g of sodium hydroxide and 30 ml of water. Then the whole is cooled to room temperature, 20 ml of acetone are added and 1.2 g of glacial acetic -chlorobenzamido>-ethyl)-benzenesulfonyl] acid, and 4.1 g of 2-methoxy-5-chlorobenzoylchloride are added in portions and stirring is continued for 1 hour. The precipitate if filtered off with suction, stirred with bicarbonate solution and recrystallized from methanol/dimethylformamide. The N-[4-(β-<-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-N'-(4-chlorocyclohexyl)-urea obtained melts at 178°-179°C.

Workup

  1. filtrationThe precipitate if filtered off with suction
  2. stirringstirred with bicarbonate solution
  3. customrecrystallized from methanol/dimethylformamide

Sources & evidence

ORD record
ord-3a93ce9f233441f9a4c042a988c3a7d6
Source dataset
uspto-grants-1976_01
Patent number
US03932503

Reaction notes

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