Ethanone, 1-[4-(1,1-dimethylethyl)phenyl]-, oxime → 4-[2-[(E)-1-(4-tert-butylphenyl)ethylideneamino]oxyethoxy]-3-chlorobenzoic acid
Reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12]Br)=[C:6]([Cl:14])[CH:5]=1.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26](=[N:28][OH:29])[CH3:27])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>>[C:16]([C:20]1[CH:25]=[CH:24][C:23](/[C:26](=[N:28]/[O:29][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:15])=[CH:5][C:6]=2[Cl:14])/[CH3:27])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]Participants
3
Procedure
The title compound was prepared as white solid (0.334 g, 53%) from 4-(2-bromo-ethoxy)-3-chloro-benzoic acid methyl ester and 1-(4-tert-butyl-phenyl)-ethanone oxime using a procedure similar to that of step 1 of example 6. mp=167.1-168.8° C.; mass spectrum (+APCI, M+H) m/z 390. 1H NMR (400 MHz, DMSO-d6); δ 12.95 (bs, 1H), 7.89 (d, 1H), 7.84 (dd, 1H), 7.57 (d, 2H), 7.39 (d, 2H), 7.29 (d, 1H), 4.45 (m, 4H), 2.13 (s, 3H), 1.29 (s, 9H). Elemental analysis: Calcd. for C21H24ClNO4: C, 64.69; H, 6.20; N, 3.59, Found: C, 64.50; H, 6.28; N, 3.57.
Sources & evidence
- ORD record
- ord-d862e08d43f94fcd8eb2d7d9ac450d41
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420083B2
Reaction notes
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