Methanesulfonyl chloride → HCID 18511545, compound

HRID 1819816Notes

Reaction equation

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

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 18511576HCID 18511576, compound

Product 1

HCID 18511545HCID 18511545, compound

Procedure

2-Chloro-N-[4-(6-methanesulfonylamino-benzothiazol-2-yloxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide was synthesized from N-[4-(6-amino-benzothiazol-2-yloxy)-phenyl]-2-chloro-4-trifluoromethyl-benzenesulfonamide (448) and methanesulfonyl chloride (Aldrich) in a similar manner as described in Examples 70-91. 1H NMR (400 MHz, DMSO-d6) δ 11.07 (s, 1H), 9.82 (s, 1H), 8.26 (d, J=8.2 Hz, 1H), 8.16 (d, J=1.1 Hz, 1H), 7.95 (dd, J=8.3, 1.2 Hz, 1H), 7.75 (d, J=2.2 Hz, 1H), 7.62 (d, J=8.7 Hz, 1H), 7.37-7.34 (m, 2H), 7.24 (dd, J=8.7, 2.2 Hz, 1H), 7.23-7.19 (m, 2H). MS (EI): m/z 576 (M−H).

Sources & evidence

ORD record: ord-b4fbf613272e4500ab8cc5b5ff3dbe87
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601841B2

Reaction notes

Loading…