Methanesulfonyl chloride → 2-Chloro-N-[3,5-dichloro-4-(6-methanesulfonylamino-benzothiazol-2-yloxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide
Reaction equation
[NH2:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]=[C:7]([O:9][C:10]3[C:15]([Cl:16])=[CH:14][C:13]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=4[Cl:31])(=[O:20])=[O:19])=[CH:12][C:11]=3[Cl:32])[S:8][C:4]=2[CH:3]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>>[Cl:31][C:22]1[CH:23]=[C:24]([C:27]([F:28])([F:30])[F:29])[CH:25]=[CH:26][C:21]=1[S:18]([NH:17][C:13]1[CH:14]=[C:15]([Cl:16])[C:10]([O:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([NH:1][S:36]([CH3:35])(=[O:38])=[O:37])[CH:34]=[CH:33][C:5]=3[N:6]=2)=[C:11]([Cl:32])[CH:12]=1)(=[O:20])=[O:19]Participants
3
Procedure
2-Chloro-N-[3,5-dichloro-4-(6-methanesulfonylamino-benzothiazol-2-yloxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide was synthesized from N-[4-(6-Amino-benzothiazol-2-yloxy)-3,5-dichloro-phenyl]-2-chloro-4-trifluoromethyl-benzenesulfonamide (439) and methanesulfonyl chloride (Aldrich) in a similar manner as described in Examples 70-91. 1H NMR (400 MHz, DMSO-d6) δ 11.64 (s, 1H), 9.87 (s, 1H), 8.38 (d, J=8.3 Hz, 1H), 8.22 (s, 1H), 8.00 (d, J=8.2 Hz, 1H), 7.83 (d, J=1.8 Hz, 1H), 7.62 (d, J=8.8 Hz, 1H), 7.31 (s, 2H), 7.23 (dd, J=8.8, 1.5 Hz, 1H). MS (EI): m/z 644 (M−H).
Sources & evidence
- ORD record
- ord-5f1e35d5003149e1ae8232db2b44e6c4
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06583157B2
Reaction notes
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