2,1,3-Benzothiadiazole, 4-chlorosulfonyl- → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methylbenzoic acid methyl ester

HRID 2265189Notes

Reaction equation

HRID 2265189 reaction equation
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10](Cl)(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[NH2:24]>>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[NH:24][S:10]([C:6]1[C:3]2=[N:4][S:5][N:1]=[C:2]2[CH:9]=[CH:8][CH:7]=1)(=[O:12])=[O:11]

Participants

3

Reactant 2

HCID 27354592,1,3-Benzothiadiazole, 4-chlorosulfonyl-HCID 11205965Methyl 2-amino-4-methylbenzoate

Product 1

HCID 687707252-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methylbenzoic acid methyl esterYield 53%

Procedure

The title compound (1.22 g, 53%) was prepared from benzo[1,2,5]thiadiazole-4-sulfonyl chloride and 2-amino-4-methyl-benzoic acid methyl ester as in Example 10, Part A. 1H NMR (500 MHz, CDCl3): 11.28 (s, 1H), 8.36 (dd, J=7.1, 1.0, 1H), 8.19 (dd, J=8.8, 1.0, 1H), 7.73 (d, J=8.1, 1H), 7.68 (dd, J=8.8, 7.1, 1H), 7.51 (br s, 1H), 6.77 (dd, J=8.1, 0.9, 1H), 3.89 (s, 3H), 2.28 (s, 3H).

Sources & evidence

ORD record
ord-5c44e3e1eed445e0b362f640eca8d37d
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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