N-[(4-tert-butylphenyl)methylidene]hydroxylamine → 4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]-2-[[2-(trifluoromethyl)benzoyl]amino]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].[C:29]([C:33]1[CH:41]=[CH:40][C:36]([CH:37]=[N:38][OH:39])=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30]>>[C:29]([C:33]1[CH:41]=[CH:40][C:36](/[CH:37]=[N:38]/[O:39][CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:28])=[C:5]([NH:15][C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:24])([F:26])[F:25])[CH:6]=2)=[CH:35][CH:34]=1)([CH3:32])([CH3:30])[CH3:31]Participants
3
Reactant 2
Product 1
Procedure
The title compound (0.117 g, 64%) was prepared as a white solid from 4-(3-bromo-propoxy)-2-(2-trifluoromethyl-benzoylamino)-benzoic acid methyl ester and 4-tert-butyl-benzaldehyde oxime using a procedure similar to step 1 of example 6. mp=121.1-122.0° C.; mass spectrum API-ES, (M−H) m/z 541. 1H NMR (400 MHz, DMSO-d6); δ 13.40 (bs, 1H), 11.90 (bs, 1H), 8.28 (d, 1H), 8.22 (s, 1H), 7.96 (d, 1H), 7.88 (d, 1H), 7.80 (m, 3H), 7.50 (d, 2H), 7.39 (d, 2H), 6.82 (dd, 1H), 4.28 (t, 2H), 4.18 (t, 2H), 2.15 (m, 2H), 1.25 (s, 9H). Elemental analysis: Calcd. for C29H29F3N2O5: C, 62.2; H, 5.39; N, 5.16, Found: C, 63.8; H, 5.26; N, 5.04.
Sources & evidence
- ORD record
- ord-396af70deeba4a9fb4181d9bd23cf04c
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420083B2
Reaction notes
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