3-(Trifluoromethyl)aniline → 3-hydroxy-N-[3-(trifluoromethyl)phenyl]-1-benzothiophene-2-carboxamide

HRID 2292003Notes

Reaction equation

HRID 2292003 reaction equation
[OH:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([O:13]C)=O.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>CCOCC>[OH:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([NH:20][C:19]1[CH:21]=[CH:22][CH:23]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=1)=[O:13]

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 83165Methyl 3-hydroxybenzo(b)thiophene-3-carboxylate

Product 1

HCID 9013113-hydroxy-N-[3-(trifluoromethyl)phenyl]-1-benzothiophene-2-carboxamideYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of methyl 3-hydroxy-benzothiophene2-carboxylate (1.04 g; 0.005M) and 3-trifluoromethylaniline (1.61 g; 0.010M) is heated under a nitrogen atmosphere at 170° C. for 90 minutes. and then at 200° C. for 30 minutes. The reaction was cooled at room temperature, taken up in ether and the solid was collected, washed with ether and air dried. The solid was recrystallized from ethyl acetate to give 0.96 g (57% yield) of the title compound; m.p. 205°-208° C. (dec).

Workup

  1. temperatureThe reaction was cooled at room temperature
  2. customthe solid was collected
  3. washwashed with ether and air
  4. customdried
  5. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-450c729a50544b858f417ca9680831c7
Source dataset
uspto-grants-1989_01
Patent number
US04800211

Reaction notes

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