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

HRID 2253464Notes

Reaction equation

HRID 2253464 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.[C:28]1([CH3:38])[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([NH2:37])(=[O:36])=[O:35])[CH:29]=1>>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([NH:37][S:34]([C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([CH3:38])[CH:29]=3)(=[O:35])=[O:36])=[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 74697m-ToluenesulphonamideHCID 30361523-[4-(Z)-(1,2-diphenylbut-1-enyl)phenyl]-acrylic acid

Product 1

HCID 69781095N-{3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-3-methyl-benzenesulfonamide

Procedure

Prepared by coupling 1a and m-toluenesulfonamide (Synlett, 1997, 375) in accordance with Procedure 1, Method B described hereinabove. Yield (24%); 1H NMR (CDCl3) δ 7.86 (m, 2H), 7.50 (d, J=15.7 Hz, 1H), 7.42-7.07 (m, 14H), 6.86 (d, J=8.4 Hz, 2H), 6.27 (d, J=15.7 Hz, 1H), 2.47 (q, J=7.3 Hz, 2H), 2.41 (s, 3H), 0.93 (t, J=7.3 Hz, 3H); APcI m/z: 508 (M+H+).

Workup

  1. customPrepared
  2. customYield (24%)

Sources & evidence

ORD record
ord-95cfd11335834de5af7b1b3a8cae8775
Source dataset
uspto-grants-2008_01
Patent number
US07323587B2

Reaction notes

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