2-(Trifluoromethyl)benzoyl chloride → HCID 90229342, compound

HRID 1505759Notes

Reaction equation

HRID 1505759 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:10]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20]>C1COCC1.C(N(CC)C(C)C)(C)C>[F:15][C:16]([F:26])([F:27])[C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([NH:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:10]=1)=[O:20]

Participants

5

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 84663096HCID 84663096, compound

Product 1

HCID 90229342HCID 90229342, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of methyl 6-amino-1H-benzimidazole-4-carboxylate (266 mg) in dehydrated THF (12 mL), N,N-diisopropylethylamine (284 μL) was added, and the solution was stirred under ice-cooling. To this solution, 2-(trifluoromethyl)benzoyl chloride (284 μL) in dehydrated THF (5 mL) was added slowly dropwise, and stirred at the same temperature for 3 hours. After ice water was added, THF was removed under reduced pressure, and aqueous saturated sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on NH silica gel column chromatography (ethyl acetate→ethyl acetate/MeOH) to obtain the titled compound (309 mg) as pale yellow powder.

Workup

  1. temperaturecooling
  2. stirringstirred at the same temperature for 3 hours
  3. customTHF was removed under reduced pressure, and aqueous saturated sodium bicarbonate
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified on NH silica gel column chromatography (ethyl acetate→ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-1f5ecb7c333c4461a9b89f2e3db07ce4
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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