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

HRID 614180Notes

Reaction equation

HRID 614180 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-3dc59a7c9a8540cf9ab02744def46396
Source dataset
uspto-grants-1979_03
Patent number
US04144047

Reaction notes

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