Dimethylformamide → HCID 18522082, compound

HRID 413749Notes

Reaction equation

HRID 413749 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]([CH2:17][C:16]3[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=3)[C:2](=[NH:1])[N:3]([CH2:17][C:16]3[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=3)[C:4]=2[CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 215271H-Benzimidazol-2-amine, 5-chloro-

Product 1

HCID 18522082HCID 18522082, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-amino-5-chloro-benzimidazole (9.4 g, 56.1 mmol), 4-chlorobenzylchloride (9.93 g, 61.7 mmol), potassium carbonate (15.5 g, 112 mmol) and dimethyl formamide (150 ml) was stirred at 50° C. for 20 h. Water (150 ml) was added and the product was filtered off. The crude product was purified by chromatography using silica gel and a mixture of ethanol (5%) and dichloromethane as eluent. The product was isolated as the free base. Yield 0.37 g, 2%. M.p. 175-177° C.

Workup

  1. filtrationthe product was filtered off
  2. customThe crude product was purified by chromatography
  3. additiona mixture of ethanol (5%) and dichloromethane as eluent
  4. customThe product was isolated as the free base

Sources & evidence

ORD record
ord-9417fcc6daed47fb85cfeaaeefcd26c6
Source dataset
uspto-grants-2003_05
Patent number
US06569880B2

Reaction notes

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