Benzene, 1-chloro-3-isocyanato- → HCID 86736252, compound

HRID 2163668Notes

Reaction equation

HRID 2163668 reaction equation
[N+:1]([C:4]1[O:19][C:7]([CH:8]=[C:9]2[N:13]=[C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([NH2:18])[C:11]3=[N:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:20][C:21]1[CH:22]=[C:23]([N:27]=[C:28]=[O:29])[CH:24]=[CH:25][CH:26]=1>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]([N:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([NH2:18])[C:11]=3[NH:10][C:9]2=[CH:8][C:7]2[O:19][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:29])[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 70604281HCID 70604281, compound

Product 1

HCID 86736252HCID 86736252, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

51.2 g of 2-(5-nitro-furfurylidene)-amino-benzimidazole are dissolved in a mixture of 120 ml of chloroform and 80 ml of dimethylformamide, whereupon 30.6 g (0.2 moles) of 3-chlorophenyl-isocyanate are slowly added. The crystalline reaction mixture is stirred at room temperature for 7 hours while a mixture of 40 ml of dimethylformamide and 60 ml of chloroform are added. The precipitated crystals are filtered off, washed with 100 ml of chloroform and dried in vacuo at 40° C. to 60° C. Thus 54 g of 1-(3'-chlorophenyl-carbamoyl)-2-(5-nitro-furfurylidene)-amino-benzimidazole are obtained. Mp.: 210°-212° C.

Workup

  1. additionare slowly added
  2. additionare added
  3. filtrationThe precipitated crystals are filtered off
  4. washwashed with 100 ml of chloroform
  5. customdried in vacuo at 40° C. to 60° C

Sources & evidence

ORD record
ord-e18b0b2b2649405d8434f0b80d062e79
Source dataset
uspto-grants-1979_01
Patent number
US04136189

Reaction notes

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