4-Phenylbenzaldoxime → 4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[2-(trifluoromethyl)benzoyl]amino]benzoic acid

HRID 29666Notes

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]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:34]=[CH:33][C:32]([CH:35]=[N:36][OH:37])=[CH:31][CH:30]=1>>[C:29]1([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:30]=[CH:31][C:32](/[CH:35]=[N:36]/[O:37][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:25])([F:26])[F:24])[CH:6]=2)=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 2615464-Phenylbenzaldoxime

HCID 692055024-(3-Bromo-propoxy)-2-(2-trifluoromethyl-benzoylamino)-benzoic acid methyl ester

Product 1

HCID 114329774-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[2-(trifluoromethyl)benzoyl]amino]benzoic acidYield 92%

Procedure

The title compound (0.193 g, 92%) was prepared as a white solid from 4-(3-bromo-propoxy)-2-(2-trifluoromethyl-benzoylamino)-benzoic acid methyl ester and Biphenyl-4-carbaldehyde oxime using a procedure similar to step 1 of example 6. mp=170.5-172.5° C.; mass spectrum API-ES, (M−H) m/z 561. 1H NMR (400 MHz, DMSO-d6); δ 13.40 (bs, 1H), 12.00 (bs, 1H), 8.32 (s, 1H), 8.27 (d, 1H), 7.98 (d, 1H), 7.88 (d, 1H), 7.81 (m, 2H), 7.76 (m, 1H), 7.68 (m, 6H), 7.46 (m, 2H), 7.38 (m, 1H), 6.82 (dd, 1H), 4.32 (t, 2H), 4.20 (t, 2H), 2.20 (m, 2H). Elemental analysis: Calcd. for C31H25F3N2O5: C, 66.19; H, 4.48; N, 4.98, Found: C, 65.26; H, 4.49; N, 4.77.

Sources & evidence

ORD record: ord-b49eb42f50024e2da2af8261e70efb0f
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420083B2

Reaction notes

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