Methyl 2-amino-5-chlorobenzoate → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-benzoic acid methyl ester

HRID 2265203Notes

Reaction equation

HRID 2265203 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]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[NH2:24]>>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[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 78878Methyl 2-amino-5-chlorobenzoateHCID 27354592,1,3-Benzothiadiazole, 4-chlorosulfonyl-

Product 1

HCID 687725992-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-benzoic acid methyl esterYield 75%

Procedure

The title compound (1.56 g, 75%) was prepared from benzo[1,2,5]thiadiazole-4-sulfonyl chloride and 2-amino-5-chloro-benzoic acid methyl ester as in Example 1, Part A. HPLC: RT=10.77 min. MS (ESI+): mass calcd. for C14H10ClN3O4S2, 382.98; m/z found, 406 [M+Na]+. 1H NMR (500 MHz, CDCl3): 11.16 (s, 1H), 8.35 (dd, J=7.0, 1.0, 1H), 8.22 (dd, J=8.8, 1.0, 1H), 7.82 (d, J=2.5, 1H), 7.72-7.68 (m, 2H), 7.34 (dd, J=9.0, 2.5, 1H), 3.92 (s, 3H).

Sources & evidence

ORD record
ord-efd9723da9724576b1e6a787a27a430d
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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