4-(Trifluoromethyl)aniline → HCID 67526351, compound

HRID 133760Notes

Reaction equation

HRID 133760 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH3:12][C:13]1[CH:14]=[C:15]([NH:22][C:23]([C:25]2([CH3:28])[CH2:27][O:26]2)=[O:24])[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20]>>[OH:26][C:25]([CH3:28])([CH2:27][NH:7][C:6]1[CH:8]=[CH:9][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][CH:5]=1)[C:23]([NH:22][C:15]1[CH:16]=[CH:17][C:18]([N+:19]([O-:21])=[O:20])=[C:13]([CH3:12])[CH:14]=1)=[O:24]

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 714200032-Methyl-N-(3-methyl-4-nitrophenyl)oxirane-2-carboxamide

Product 1

HCID 67526351HCID 67526351, compound

Procedure

2-Hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)-3-(4-trifluoromethylphenylamino)propionamide was prepared as described in Example 52 starting from 4-(trifluoromethyl)aniline and 2-methyloxirane-2-carboxylic acid (3-methyl-4-nitrophenyl)amide. The crude product was purified by flash chromatography (dichloromethane-1.5% methanol). 1H NMR (400 MHz, DMSO-d6): 1.42 (3H, s), 2.51 (3H, s), 3.23 (1H, dd, J=13.3 Hz, J=5.0 Hz), 3.51 (1H, dd, J=13.3 Hz, J=7.0 Hz), 6.06 (1H, s), 6.18 (1H, m), 6.77 (2H, d, J=8.4 Hz)), 7.31 (2H, d, J=8.4 Hz), 7.79-7.83 (2H, m), 8.01 (1H, d, J=8.9 Hz), 10.02 (1H, s).

Workup

  1. customThe crude product was purified by flash chromatography (dichloromethane-1.5% methanol)

Sources & evidence

ORD record
ord-2ec93779f3424fabbbd1f5a18ebfa23c
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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