Hydrochloric Acid → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methylbenzoic acid

HRID 2265190Notes

Reaction equation

HRID 2265190 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[NH:11][S:12]([C:15]1[C:20]2=[N:21][S:22][N:23]=[C:19]2[CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13].O[Li].O.Cl>C1COCC1.O>[N:23]1[S:22][N:21]=[C:20]2[C:15]([S:12]([NH:11][C:5]3[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]=3[C:3]([OH:24])=[O:2])(=[O:13])=[O:14])=[CH:16][CH:17]=[CH:18][C:19]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 687707252-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methylbenzoic acid methyl ester

Product 1

HCID 687710222-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methylbenzoic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-methylbenzoic acid methyl ester (1.22 g, 3.36 mmol) in 3:1 THF/water (10 mL) was treated with LiOH.H2O (1.41 g, 33.6 mmol) and was stirred at rt for 16 h. The mixture was acidified with 1 N HCl, and the resulting precipitate was collected by filtration, washing with water. Drying in air provided the title acid as a tan solid (0.89 g, 2.5 mmol, 74%). 1H NMR (500 MHz, CDCl3): 11.16 (s, 1H), 8.38 (dd, J=7.0, 1.0, 1H), 8.22 (dd, J=8.8, 1.0, 1H), 7.84 (d, J=8.1, 1H), 7.71 (dd, J=8.8, 7.1, 1H), 7.56 (br s, 1H), 6.83 (br d, J=8.4, 1H), 2.32 (s, 3H).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashing with water
  3. customDrying in air

Sources & evidence

ORD record
ord-5344d35b03ed471283df6404b79b10ce
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

Loading…