Methanesulfonyl chloride → HCID 18511618, compound

HRID 2422478Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([O:10][C:11]3[C:16]([Cl:17])=[CH:15][C:14]([NH:18][S:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=4[Cl:32])(=[O:21])=[O:20])=[CH:13][C:12]=3[Cl:33])=[N:7][C:6]=2[CH:34]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>>[Cl:32][C:23]1[CH:24]=[C:25]([C:28]([F:29])([F:30])[F:31])[CH:26]=[CH:27][C:22]=1[S:19]([NH:18][C:14]1[CH:15]=[C:16]([Cl:17])[C:11]([O:10][C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:36]([CH3:35])(=[O:38])=[O:37])=[CH:34][C:6]=3[N:7]=2)=[C:12]([Cl:33])[CH:13]=1)(=[O:21])=[O:20]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 18511534HCID 18511534, compound

Product 1

HCID 18511618HCID 18511618, compound

Procedure

2-Chloro-N-[3,5-dichloro-4-(5-methanesulfonylamino-benzothiazol-2-yloxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide was synthesized from N-[4-(5-Amino-benzothiazol-2-yloxy)-3,5-dichloro-phenyl]-2-chloro-4-trifluoromethyl-benzenesulfonamide (456) and methanesulfonyl chloride (Aldrich) in a similar manner as described in Examples 70-91. 1H NMR (400 MHz, DMSO-d6) δ 11.63 (s, 1H), 9.87 (s, 1H), 8.38 (d, J=8.3 Hz, 1H), 8.20 (s, 1H), 8.00 (d, J=8.3 Hz, 1H), 7.91 (d, J=8.6 Hz, 1H), 7.44 (d, J=1.7 Hz, 1H), 7.32 (s, 2H), 7.21 (dd, J=8.7, 1.6 Hz, 1H). MS (EI): m/z 644 (M−H).

Sources & evidence

ORD record: ord-a5cf0b5f2c3b4382a5c2e8d1cb425336
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960408B2

Reaction notes

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