3,4-Dichlorophenyl isocyanate → HCID 86736253, compound

HRID 2163669Notes

Reaction equation

HRID 2163669 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:28]=[C:29]=[O:30])[CH:24]=[CH:25][C:26]=1[Cl:27]>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:20][C:21]1[CH:22]=[C:23]([NH:28][C:29]([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:30])[CH:24]=[CH:25][C:26]=1[Cl:27]

Participants

5

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 70604281HCID 70604281, compound

Product 1

HCID 86736253HCID 86736253, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

51.2 g (0.2 moles) 2-(5-nitro-furfurylidene)-amino-benzimidazole are stirred in a mixture of 120 ml of chloroform and 80 ml of dimethylformamide, whereupon 37.6 g (0.2 moles) of powdered 3.4-dichlorophenyl-isocyanate are 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 70 g of 1-(3',4'-dichlorophenyl-carbamoyl)-2-(5-nitro-furfurylidene)-amino-benzimidazole are obtained. Mp.: 202°-204° C.

Workup

  1. additionare 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-3f96e52d58a847f8af3f9c88cbff45bb
Source dataset
uspto-grants-1979_01
Patent number
US04136189

Reaction notes

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