3-Chlorobenzenesulfonamide → 3-chloro-N-{3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-benzenesulfonamide

HRID 1824880Notes

Reaction equation

HRID 1824880 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.[Cl:28][C:29]1[CH:30]=[C:31]([S:35]([NH2:38])(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>>[Cl:28][C:29]1[CH:30]=[C:31]([S:35]([NH:38][C:25](=[O:26])[CH:24]=[CH:23][C:20]2[CH:21]=[CH:22][C:17]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][CH3:10])=[CH:18][CH:19]=2)(=[O:36])=[O:37])[CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 5193773-ChlorobenzenesulfonamideHCID 30361523-[4-(Z)-(1,2-diphenylbut-1-enyl)phenyl]-acrylic acid

Product 1

HCID 693159973-chloro-N-{3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-benzenesulfonamide

Procedure

Prepared by coupling 1a and 3-chlorobenzenesulfonamide in accordance with Procedure 1, Method B described hereinabove. Yield (25%); 1H NMR (d6-DMSO) δ 12.36 (s, 1H), 7.88–7.76 (m, 3H), 7.63 (t, J=8.1 Hz, 1H), 7.42–7.07 (m, 13H), 6.84 (d, J=8.0 Hz, 2H), 6.40 (d, J=15.7 Hz, 1H), 2.36 (q, J=7.3 Hz, 2H), 0.82 (t, J=7.3 Hz, 3H); APcI m/z: 527 (M−H−).

Workup

  1. customPrepared
  2. customYield (25%)

Sources & evidence

ORD record
ord-070134cd367349db9cc6d792cf5caf58
Source dataset
uspto-grants-2006_05
Patent number
US07045540B2

Reaction notes

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