Ammonia → N'-(4-chlorocyclohexyl)-urea

HRID 1580323Notes

Reaction equation

HRID 1580323 reaction equation
[Na].C1(S(N)(=O)=O)C=CC=CC=1.C1([N:18](C2C=CC=CC=2)[C:19]([NH:21][CH:22]2[CH2:27][CH2:26][CH:25]([Cl:28])[CH2:24][CH2:23]2)=[O:20])C=CC=CC=1.CN(C)C=O.N>O>[Cl:28][CH:25]1[CH2:24][CH2:23][CH:22]([NH:21][C:19](=[O:20])[NH2:18])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 21534940N'-(4-Chlorocyclohexyl)-N,N-diphenylureaHCID 24194900Benzenesulfonamide sodium

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.9 g of 4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonamide sodium, 6.5 g of N.N-diphenyl-N'-(4-chlorocyclohexyl)-urea (melting point 115° -116°C) and 100 ml dimethyl formamide are heated to 110°C for 45 minutes. Then the whole is cooled, poured into water and ammonia of 1 % strength is added. Then the whole is filtered, the filtrate is acidified and the precipitate obtained is purified once more over ammonia/hydrochloric acid. The N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-N'-(4-chlorocyclohexyl)-urea precipitating in crystalline form melts at 178° -179°C after recrystallization from methanol/dimethylformamide.

Workup

  1. temperatureThen the whole is cooled
  2. additionis added
  3. filtrationThen the whole is filtered
  4. customthe precipitate obtained
  5. customis purified once more over ammonia/hydrochloric acid

Sources & evidence

ORD record
ord-8db83948de2b4cfda790e1912a6233da
Source dataset
uspto-grants-1976_01
Patent number
US03932503

Reaction notes

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