2,1,3-Benzothiadiazole, 4-chlorosulfonyl- → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-benzoic acid methyl ester
Reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[S:14]([C:17]1[C:25]2[C:21](=[N:22][S:23][N:24]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15]>>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([Br:12])=[CH:11][C:2]=1[NH:1][S:14]([C:17]1[C:25]2=[N:24][S:23][N:22]=[C:21]2[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15]Participants
3
Procedure
The title compound (3.95 g, 75%) was prepared from methyl 2-amino-4-bromobenzoate and 4-chlorosulfonyl-2,1,3-benzothiadiazole as in Example 1, Part A. MS (ESI−): mass calcd. for C14H10BrN3O4S2, 426.9; m/z found, 426 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.34 (br s, 1H), 8.40 (dd, J=7.0, 0.9, 1H), 8.24 (dd, J=8.8, 0.9, 1H), 7.92 (d, J=1.8, 1H), 7.74 (dd, J=8.8, 7.0, 1H), 7.72 (d, J=8.5, 1H), 7.10 (dd, J=8.5, 1.8, 1H), 3.92 (s, 3H).
Sources & evidence
- ORD record
- ord-6f4f707d50d04fa2a475a820cf420600
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855292B2
Reaction notes
Loading…