Hydrochloric Acid → 2-[(2,1,3-Benzothiadiazol-4-ylsulfonyl)amino]-5-chlorobenzoic acid

HRID 2265204Notes

Reaction equation

HRID 2265204 reaction equation
O[Li].O.C[O:5][C:6](=[O:27])[C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[NH:14][S:15]([C:18]1[C:23]2=[N:24][S:25][N:26]=[C:22]2[CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16].Cl>C1COCC1.O>[N:26]1[S:25][N:24]=[C:23]2[C:18]([S:15]([NH:14][C:8]3[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=3[C:6]([OH:27])=[O:5])(=[O:17])=[O:16])=[CH:19][CH:20]=[CH:21][C:22]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 687725992-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-benzoic acid methyl ester

Product 1

HCID 28320372-[(2,1,3-Benzothiadiazol-4-ylsulfonyl)amino]-5-chlorobenzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (0.68 g, 16.2 mmol) was added to a stirred solution of 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-benzoic acid methyl ester (1.56 g, 4.06 mmol) in THF (15 mL) and water (5 mL). After 18 h, the solution was acidified to pH 2 with conc. HCl, diluted with water, and extracted with DCM (3×). The combined organic layers were dried (MgSO4), and concentrated to provide the title compound (1.50 g, 100%). HPLC: RT=9.48 min. MS (ESI−): mass calcd. for C13H8ClN3O4S2, 368.96; m/z found, 368/370 [M−H]. 1H NMR (500 MHz, CDCl3): 11.07 (s, 1H), 8.38 (dd, J=7.0, 1.0, 1H), 8.24 (dd, J=8.8, 1.0, 1H), 7.92 (d, J=2.5, 1H), 7.75 (d, J=9.0, 1H), 7.71-7.69 (m, 1H), 7.40 (dd, J=9.0, 2.6, 1H).

Workup

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9f21e363f6274f8f9f639a8971ce46d7
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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