Sodium Hydroxide → 3-(m-Tolyl)-4,5-Isothiazoledicarboxylic Acid

HRID 1448682Notes

Reaction equation

HRID 1448682 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:11]([C:12]([O:14]C)=[O:13])=[C:10]([C:16]([O:18]C)=[O:17])[S:9][N:8]=2)[CH:2]=1.[OH-].[Na+]>O>[C:1]1([CH3:20])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:11]([C:12]([OH:14])=[O:13])=[C:10]([C:16]([OH:18])=[O:17])[S:9][N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12437411Dimethyl 3-(m-Tolyl)-4,5-Isothiazoledicarboxylate

Product 1

HCID 124374313-(m-Tolyl)-4,5-Isothiazoledicarboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl 3-(m-tolyl)-4,5-isothiazoledicarboxylate (14.03 g, 0.0548 mol) was hydrolyzed in NaOH (10.96 g, 0.274 mol) and 50 ml H2O for 0.5 hours at reflux. Acidification with HCl, extraction with ether and recrystallization gave a light yellow solid, m.p. 166.5°-167° with decomposition.

Workup

  1. extractionAcidification with HCl, extraction
  2. customwith ether and recrystallization
  3. customgave a light yellow solid, m.p. 166.5°-167° with decomposition

Sources & evidence

ORD record
ord-3f25c2689c9d4204a2c1f0ee57157080
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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