3-(Trifluoromethyl)aniline → 1-[(5-Chloro-1-benzothien-3-YL)methyl]-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-one

HRID 1988817Notes

Reaction equation

HRID 1988817 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][N:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=O)[C:12]3=[O:21])[C:6]=2[CH:22]=1.[F:23][C:24]([F:33])([F:32])[C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][N:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=[N:28][C:27]4[CH:29]=[CH:30][CH:31]=[C:25]([C:24]([F:23])([F:32])[F:33])[CH:26]=4)[C:12]3=[O:21])[C:6]=2[CH:22]=1

Participants

3

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 220224531-[(5-chloro-1-benzothien-3-yl)methyl]-2H-indole-2,3-dione

Product 1

HCID 220224461-[(5-Chloro-1-benzothien-3-YL)methyl]-3-{[3-(trifluoromethyl)phenyl]imino}-1,3-dihydro-2H-indol-2-oneYield 20%

Conditions

Temperature
140 °C

Procedure

A mixture of 1-[(5-chloro-1-benzothien-3-yl)methyl]-2H-indole-2,3-dione (50 mg, 0.15 mmol) and 3-trifluoromethylaniline (0.020 mL, 0.15 mmol) was heated neat at 140° C. for 2 h. The crude material was purified by preparative TLC using a mixture of 1:3 ethyl acetate and hexane as the eluent giving the desired product as a yellow solid (13 mg, 0.030 mmol, 18%).

Workup

  1. customThe crude material was purified by preparative TLC
  2. additiona mixture of 1:3 ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-f524216d7b834e998a2ec014f39b33f1
Source dataset
uspto-grants-2010_01
Patent number
US07642281B2

Reaction notes

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