4-Fluorophenol → N-(4-Cyano-3-methylphenyl)-3-(4-fluorophenoxy)-2-hydroxy-2-methylpropionamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2([CH3:23])[CH2:22][O:21]2)=[O:19])=[CH:13][C:12]=1[CH3:24])#[N:10]>>[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:19])[C:20]([OH:21])([CH3:22])[CH2:23][O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:13][C:12]=1[CH3:24])#[N:10]Participants
3
Procedure
N-(4-Cyano-3-methylphenyl)-3-(4-fluorophenoxy)-2-hydroxy-2-methylpropionamide was prepared as described in Example 1 starting from 4-fluorophenol and 2-methyl-oxirane-2-carboxylic acid (4-cyano-3-methylphenyl)amide. 1H NMR (DMSO-d6): 1.42 (3H, s), 2.44 (3H, s), 3.94 (1H, d, J=9.6 Hz), 4.18 (1H, d, J=9.6 Hz), 6.18 (1H, bs), 6.93 (2H, m), 7.08 (2H, m), 7.69 (1H, d, J=9.0 Hz), 7.78 (1H, dd, J=9.0 Hz and 2.1 Hz), 7.93 (1H, d, J=2.1 Hz), 10.02 (1H, s).
Sources & evidence
- ORD record
- ord-1148d3301d9f4214af0e2dd35315a3fb
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07390923B2
Reaction notes
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