Benzimidazole → Ethyl 2-(1H-benzimidazol-1yl)-4-(trifluoromethyl)5-oxazolecarboxylate

HRID 619881Notes

Reaction equation

HRID 619881 reaction equation
Cl[C:2]1[O:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH:18][CH:17]=1>C(OCC)C>[N:16]1([C:2]2[O:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[CH:17]1

Participants

4

Reactant 2

HCID 5798BenzimidazoleHCID 12785855Ethyl 2-chloro-4-(trifluoromethyl)oxazole-5-carboxylate

Product 1

HCID 14672732Ethyl 2-(1H-benzimidazol-1yl)-4-(trifluoromethyl)5-oxazolecarboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A reaction vessel was charged with 5 g (21 mmol) ethyl 2-chloro-4-trifluoromethyl-5-oxazolecarboxylate and 4.96 g (42 mmol) benzimidazole. This mixture without solvent was heated at a temperature of about 100°-110° C. for 30 hours. The mixture was cooled to room temperature. This mixture was slurried in ethyl ether, washed with 5% hydrochloric acid, and then washed with large amounts of water, at which time a white precipitate began to form. A yellow filtrate was separated from 2.1 g of the precipitate (m.p. 133°-135° C.). The filtrate was concentrated under reduced pressure to provide 2.80 g of an off-white solid material (m.p. 132°-134° C.). This solid material and the white precipitate were combined and recrystallized from ethanol-water solution to give 4.03 g of an off-white solid product (m.p. 132°-134° C.) identified in Table I.

Workup

  1. temperatureThis mixture without solvent was heated at a temperature of about 100°-110° C. for 30 hours
  2. washwashed with 5% hydrochloric acid
  3. washwashed with large amounts of water, at which time a white precipitate
  4. customto form
  5. customA yellow filtrate was separated from 2.1 g of the precipitate (m.p. 133°-135° C.)
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e44a85417f5448bdb3a3fa127c23ee13
Source dataset
uspto-grants-1989_04
Patent number
US04818270

Reaction notes

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