3-[4-(Z)-(1,2-diphenylbut-1-enyl)phenyl]-acrylic acid → N-{3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-C-(4-trifluoromethyl-phenyl)-methanesulfonamide

HRID 1824897

Reaction equation

HRID 1824897 reaction equation
[C:1]1(/[C:7](/[C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25](O)=[O:26])=[CH:19][CH:18]=2)=[C:8](/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)\[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:28][C:29]([F:42])([F:41])[C:30]1[CH:35]=[CH:34][C:33]([CH2:36][S:37]([NH2:40])(=[O:39])=[O:38])=[CH:32][CH:31]=1>>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([NH:40][S:37]([CH2:36][C:33]3[CH:32]=[CH:31][C:30]([C:29]([F:28])([F:41])[F:42])=[CH:35][CH:34]=3)(=[O:39])=[O:38])=[O:26])=[CH:19][CH:18]=2)=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH3:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 30361523-[4-(Z)-(1,2-diphenylbut-1-enyl)phenyl]-acrylic acidHCID 221445811-[4-(Trifluoromethyl)phenyl]methanesulfonamide

Product 1

HCID 69780577N-{3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-C-(4-trifluoromethyl-phenyl)-methanesulfonamide

Procedure

Prepared by coupling 1a and [(4-trifluoromethylphenyl)-methyl]sulfonamide (Synlett, 1997, 375) in accordance with Procedure 1, Method B described hereinabove. Yield (11%); 1H NMR (d6-DMSO) δ 11.69 (br s, 1H), 7.74 (d, J=8.0 Hz, 2H), 7.57–7.09 (m, 15H), 6.87 (d, J=8.1 Hz, 2H), 6.41 (d, J=15.7 Hz, 1H), 4.86 (s, 2H), 2.37 (q, J=7.3 Hz, 2H), 0.83 (t, J=7.3 Hz, 3H); APcI m/z: 576 (M+H+).

Workup

  1. customPrepared
  2. customYield (11%)

Sources & evidence

ORD record
ord-3e4b35490e854b10b4ca9795881fe368
Source dataset
uspto-grants-2006_05
Patent number
US07045540B2

Linked notes

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