Benzimidazole → HCID 14672729, compound

HRID 619879Notes

Reaction equation

HRID 619879 reaction equation
CC(N(C)C)=O.Cl[C:8]1[S:9][C:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=1.[N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[NH:24][CH:23]=1>O>[N:22]1([C:8]2[S:9][C:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 31374DimethylacetamideHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 14672729HCID 14672729, compoundYield 287.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 150 ml dimethylacetamide, 13.0 g (50 mmol) ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate and 11.8 g (100 mmol) benzimidazole. The reaction mixture was heated at a temperature of 115°-125° C. for 96 hours. The mixture was cooled to room temperature, diluted with water and extracted three times with ethyl ether. The combined ether extracts were washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to provide 49.1 g of a dark gold oil. This oil was subjected to Kugelrohr distillation (90° C. @0.5 mm Hg) to provide 31.7 g of a yellow oil product identified in Table I.

Workup

  1. temperatureThe reaction mixture was heated at a temperature of 115°-125° C. for 96 hours
  2. extractionextracted three times with ethyl ether
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-056e7fc329e844d08ee84ebb7d96d6d6
Source dataset
uspto-grants-1989_04
Patent number
US04818270

Reaction notes

Loading…