4-Chlorophenyl Isocyanate → HCID 54055573, compound

HRID 1973922Notes

Reaction equation

HRID 1973922 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[O:17])=[CH:11][CH:10]=1>C1C=CC=CC=1>[CH3:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[N:1][C:16]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=1)=[O:17]

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 54055573HCID 54055573, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

After dissolving 14.2 g. (0.1445 mole) of 2 -imino-1 -methylpyrrolidine in anhydrous benezene, 22.2 g. (0.1445 mole) of p- chlorophenylisocyanate dissolved in anhydrous benzene is added slowly with stirring and ice-bath cooling to the above solution. Solid material forms after 10 to 15 mins. The reaction mixture is stirred at room temperature overnight. The solid is collected (m.p. = 138-141° C.) and titurated with hot CH2Cl2. The material which does not dissolve is filtered off. Removal of the methylene chloride and recrystallizations from methanol of the subsequent solid product, 1 -(1 -methyl-2 -pyrrolidylidene)-3 -p-chlorophenylurea, yields the pure material, m.p. = 142-144° C.

Workup

  1. dissolutionAfter dissolving 14.2 g
  2. additionis added slowly
  3. temperatureice-bath cooling to the above solution
  4. stirringThe reaction mixture is stirred at room temperature overnight
  5. customThe solid is collected (m.p. = 138-141° C.)
  6. dissolutionThe material which does not dissolve
  7. filtrationis filtered off
  8. customRemoval of the methylene chloride and recrystallizations from methanol of the subsequent solid product, 1 -(1 -methyl-2 -pyrrolidylidene)-3 -p-chlorophenylurea
  9. customyields the pure material, m.p. = 142-144° C.

Sources & evidence

ORD record
ord-f9fcf091841c4f82980fb3a4526a54c8
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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