Diazomethane → Methyl 3-Hydroxybenzo[d]isothiazole-6-carboxylate

HRID 1701801Notes

Reaction equation

HRID 1701801 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[S:4][NH:3]1.[N+](=[CH2:16])=[N-]>C(O)(C)C.CCOCC>[CH3:16][O:12][C:11]([C:9]1[CH:8]=[CH:7][C:6]2[C:2](=[O:1])[NH:3][S:4][C:5]=2[CH:10]=1)=[O:13]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 190767033-Oxo-1,2-benzisothiazoline-6-carboxylic acid

Product 1

HCID 19076707Methyl 3-Hydroxybenzo[d]isothiazole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 19.5 g (0.1 mole) of 3-oxo-1,2-benzisothiazoline-6-carboxylic acid in 40 ml of isopropanol is treated with an excess of a solution of diazomethane in ether added at 0° C. with stirring over a period of 10 minutes. The reaction mixture is evaporated to dryness and the 3-oxo-1,2-benzisothiazoline-6-carboxylic acid methyl ester is obtained as an oil.

Workup

  1. additionadded at 0° C.
  2. customThe reaction mixture is evaporated to dryness

Sources & evidence

ORD record
ord-420242b057044a1b96a6e31d8a4cf5fa
Source dataset
uspto-grants-1980_03
Patent number
US04195023

Reaction notes

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