4-Chlorophenyl Isocyanate → HCID 178449212, compound

HRID 2398198Notes

Reaction equation

HRID 2398198 reaction equation
Cl.Cl.[CH2:3]([NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1)=[NH:9])[CH:4]([CH3:6])[CH3:5].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1>N1C=CC=CC=1>[ClH:18].[CH2:3]([NH:7][C:8](=[NH:9])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)=[O:27])[CH:12]=1)[CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 178449211HCID 178449211, compound

Product 1

HCID 178449212HCID 178449212, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 1-isobutyl-3-m-aminophenylguanidine dihydrochloride (19.6 g.) in pyridine (100 ml.) is added dropwise a solution of p-chlorophenyl isocyanate (11.5 g.) in pyridine (25 ml.) at room temperature. The mixture is stirred for 16 hours, and the pyridine is removed by distillation under reduced pressure. The residual gum is shaken with a mixture of ether (100 ml.) and 1% aqueous sodium hydroxide solution (10 ml.) to remove pyridine hydrochloride whereafter the product crystallizes. The solid is filtered off, washed with water and ether and dried, and recrystallized from ethanol/petroleum ether b.p. 40°-60° C. to give 1-(3-isobutylguanidino)-3-(3-p-chlorophenylureido)benzene hydrochloride, m.p. 215°-216° C.

Workup

  1. customthe pyridine is removed by distillation under reduced pressure
  2. stirringThe residual gum is shaken with a mixture of ether (100 ml.) and 1% aqueous sodium hydroxide solution (10 ml.)
  3. customto remove pyridine hydrochloride whereafter the product
  4. customcrystallizes
  5. filtrationThe solid is filtered off
  6. washwashed with water and ether
  7. customdried
  8. customrecrystallized from ethanol/petroleum ether b.p. 40°-60° C.

Sources & evidence

ORD record
ord-7856c51d629144759ba0e7f143a3cd7e
Source dataset
uspto-grants-1977_05
Patent number
US04024183

Reaction notes

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