Acetic Acid → 3-Hydroxy-N-[(3-trifluoromethylphenyl)methyl]benzo[b]thiophene-2-carboxamide

HRID 2292001Notes

Reaction equation

HRID 2292001 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].C[O-].[Na+].[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([CH2:23][NH:24][C:25](=[O:28])[CH2:26]Cl)[CH:20]=[CH:21][CH:22]=1.C(O)(=O)C>CO.O>[OH:10][C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[S:4][C:26]=1[C:25]([NH:24][CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:29])[F:30])[CH:18]=1)=[O:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 10942334Sodium MethoxideHCID 212778322-Chloro-N-(3-trifluoromethyl-benzyl)-acetamide

Product 1

HCID 546938263-Hydroxy-N-[(3-trifluoromethylphenyl)methyl]benzo[b]thiophene-2-carboxamideYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl thiosalicylate (0.67 g; 0.004M) in 20 ml of methanol is added solid sodium methoxide (0.65 g; 0.012M; 3 eqv.) followed by N-[(3-trifluoromethylphenyl)methyl]-chloroacetamide (1.0 g; 0.004M) and the mixture is refluxed under a nitrogen atmosphere for 30 minutes. The mixture is cooled to room temperature and added to a solution of 1.5 ml of glacial acetic acid in 25 ml of water and cooled to 0° C. The cream colored solid is collected, washed with 50% methanol-water, air dried, and recrystallized from nitromethane to give 1.05 g (78% yield) of the title compound; m.p. 139°-141° C.

Workup

  1. temperaturethe mixture is refluxed under a nitrogen atmosphere for 30 minutes
  2. temperaturecooled to 0° C
  3. customThe cream colored solid is collected
  4. washwashed with 50% methanol-water, air
  5. customdried
  6. customrecrystallized from nitromethane

Sources & evidence

ORD record
ord-77272ecc81fe45968481f3cc40a5a03e
Source dataset
uspto-grants-1989_01
Patent number
US04800211

Reaction notes

Loading…