Acetic Acid → 1,2,3-Benzothiadiazole-7-carboxylic acid, methyl ester

HRID 1639842Notes

Reaction equation

HRID 1639842 reaction equation
[NH2:1][C:2]1[C:3]([S:12]CC2C=CC=CC=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(O)(=O)C.Cl.[N:25]([O-])=O.[Na+]>O>[S:12]1[C:3]2[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=[CH:11][C:2]=2[N:1]=[N:25]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 15430886HCID 15430886, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 1794011,2,3-Benzothiadiazole-7-carboxylic acid, methyl esterYield 65.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of methyl 3-amino-2-(benzylthio)benzoate (26.9 g, 98.4 mmol), acetic acid (1.00 L, 1.75 mol), water (200 mL) and concentrated hydrochloric acid (172 mL, 2.06 mol) was stirred at room temperature for 30 min. To the reaction mixture was added a solution of sodium nitrite (7.59 g, 110 mmol) in water (200 mL) at 0° C. and the mixture was stirred at 0-5° C. for 2 hr. The precipitate was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (12.5 g, yield 65%).

Workup

  1. stirringthe mixture was stirred at 0-5° C. for 2 hr
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-5bb3b6f64e1840c6b201613dd6565614
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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