Benzaldehyde, 4-(trifluoromethyl)-, oxime → 2-[[2-(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoic acid
Reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]Br)=[CH:6][C:5]=1[NH:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:26])([F:25])[F:24].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:39]=[CH:38][C:34]([CH:35]=[N:36][OH:37])=[CH:33][CH:32]=1>>[F:26][C:23]([F:24])([F:25])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:5]1[CH:6]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:37]/[N:36]=[CH:35]/[C:34]2[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:41])[F:40])=[CH:39][CH:38]=2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:2])=[O:28])=[O:27]Participants
3
Reactant 2
Product 1
Procedure
The title compound (0.404 g, 70%) was prepared as a white solid from 4-(3-bromo-propoxy)-2-(2-trifluoromethyl-benzoylamino)-benzoic acid methyl ester and 4-trifluoromethyl-benzaldehyde oxime using a procedure similar to step 1 of example 6. mp=147.2-147.9° C.; mass spectrum −ES, (M−H) m/z 553. 1H NMR (400 MHz, DMSO-d6); δ 13.40 (bs, 1H), 11.90 (bs, 1H), 8.38 (s, 1H), 8.26 (d, 1H), 7.97 (d, 1H), 7.86 (d, 1H), 7.77 (m, 7H), 6.81 (dd, 1H), 4.33 (t, 2H), 4.18 (t, 2H), 2.18 (m, 2H). Elemental analysis: Calcd. for C26H20F6N2O5: C, 56.32; H, 3.64; N, 5.05, Found: C, 55.83; H, 3.27; N, 4.88.
Sources & evidence
- ORD record
- ord-0ba266f398d04701b459e9eb757e539d
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420083B2
Reaction notes
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