2-Benzothiazolesulfonamide → Benzothiazole-2-sulfonic acid {3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-amide

HRID 1824898Notes

Reaction equation

HRID 1824898 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.[S:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[C:29]1[S:37]([NH2:40])(=[O:39])=[O:38]>>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([NH:40][S:37]([C:29]3[S:28][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[N:30]=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 679442-BenzothiazolesulfonamideHCID 30361523-[4-(Z)-(1,2-diphenylbut-1-enyl)phenyl]-acrylic acid

Product 1

HCID 72625150Benzothiazole-2-sulfonic acid {3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-amide

Procedure

Prepared by coupling 1a and 2-benzothiazolesulfonamide (J. Org. Chem., 1958, 1768) in accordance with Procedure 1, Method A described hereinabove. Yield (52%); 1H NMR (d6-DMSO) δ 8.07 (d, J=8.3 Hz, 1H), 7.99 (d, J=8.3 Hz, 1H), 7.53–7.05 (m, 15H), 6.78 (d, J=8.1 Hz, 2H), 6.27 (d, J=15.7 Hz, 1H), 2.35 (q, J=7.3 Hz, 2H), 0.82 (t, J=7.3 Hz, 3H); APcI m/z: 551 (M+H+)

Workup

  1. customPrepared
  2. customYield (52%)

Sources & evidence

ORD record
ord-da10f6b31e11406ea30eb26370e35259
Source dataset
uspto-grants-2006_05
Patent number
US07045540B2

Reaction notes

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