4-Chlorophenyl Isocyanate → HCID 152746826, compound

HRID 1287388Notes

Reaction equation

HRID 1287388 reaction equation
C[O-].[Na+].Cl.[C:5]([NH2:9])(=[NH:8])[CH2:6][CH3:7].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>C1C=CC=CC=1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:8][C:5](=[NH:9])[CH2:6][CH3:7])=[O:19])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 10942334Sodium MethoxideHCID 12301253Propionimidamide hydrochloride

Product 1

HCID 152746826HCID 152746826, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred, cooled mixture of 10.8 g. sodium methoxide in 100 ml. dry benzene was added 21.6 g. propionamidine hydrochloride in one portion and stirring was continued for twenty minutes. To this mixture at room temperature was added a solution of 30.6 g. of 4-chlorophenyl isocyanate in 100 ml. benzene dropwise during 15 minutes and stirring was continued for 18 hours. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. A solution of the resulting residue in either was chilled and treated with ethereal hydrogen chloride until acidic. The solid was collected by filtration to give after recrystallization from acetonitrile 22 g. of the hydrochloride of 1-(4-chlorophenyl)-3-(propanimidoyl)urea; m.p. 191°-192°C.

Workup

  1. temperatureTo a stirred, cooled
  2. additionmixture of 10.8 g
  3. waitwas continued for twenty minutes
  4. additionTo this mixture at room temperature was added a solution of 30.6 g
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated to dryness under reduced pressure
  7. temperatureA solution of the resulting residue in either was chilled
  8. additiontreated with ethereal hydrogen chloride until acidic
  9. filtrationThe solid was collected by filtration
  10. customto give
  11. customafter recrystallization from acetonitrile 22 g

Sources & evidence

ORD record
ord-fbd689ac94104341a5d662f31aee0c1f
Source dataset
uspto-grants-1976_10
Patent number
US03984467

Reaction notes

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