4-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl Chloride → 4-Bromo-N-[3,5-dichloro-4-(6-chlorobenzothiazol-2-yloxy)-phenyl]-2-trifluoromethoxy-benzenesulfonamide

HRID 2422471Notes

Reaction equation

HRID 2422471 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[C:24]([O:32][C:33]([F:36])([F:35])[F:34])[CH:23]=1>>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:20][C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([O:8][C:9]3[S:10][C:11]4[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=4[N:13]=3)=[C:6]([Cl:19])[CH:5]=2)(=[O:30])=[O:29])=[C:24]([O:32][C:33]([F:35])([F:34])[F:36])[CH:23]=1

Participants

3

Reactant 2

HCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl ChlorideHCID 221487763,5-Dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine

Product 1

HCID 185115704-Bromo-N-[3,5-dichloro-4-(6-chlorobenzothiazol-2-yloxy)-phenyl]-2-trifluoromethoxy-benzenesulfonamide

Procedure

4-Bromo-N-[3,5-dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenyl]-2-trifluoromethoxy-benzenesulfonamide was synthesized (83%) from 3,5-dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine (420) and 4-bromo-2-trifluoromethoxybenzenesulfonyl chloride (Maybridge) in a similar manner as described in Examples 70-91. 1H NMR (400 MHz, DMSO-d6) δ 11.37 (s, 1H), 8.16 (d, J=2.2 Hz, 1H), 8.03 (d, J=8.8 Hz, 1H), 7.91-7.87 (m, 2H), 7.68 (d, J=8.7 Hz, 1H), 7.47 (d, J=8.7, 2.2 Hz, 1H), 7.31 (s, 2H). MS (EI): m/z 645 (M−H).

Sources & evidence

ORD record
ord-235e871dd1c94b608229cbac3d8e5a16
Source dataset
uspto-grants-2011_06
Patent number
US07960408B2

Reaction notes

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