Hydrochloric Acid → HCID 12437439, compound

HRID 614179Notes

Reaction equation

HRID 614179 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]([C:14]([O:16]C)=[O:15])=[C:12]([C:18]([O:20]C)=[O:19])[S:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([C:18]([OH:20])=[O:19])[S:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12437419HCID 12437419, compound

Product 1

HCID 12437439HCID 12437439, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 51.9 g (0.15 mol) of dimethyl 3-(3,4-dichlorophenyl)-4,5-isothiazoledicarboxylate and 30 g (0.75 mol) of NaOH in 150 ml of water was held at reflux for 2 hours, was cooled, acidified with HCl, and was extracted with ether several times (total ether volume equals 1300 ml). The ether solution was dried (CaSO4) and concentrated to give 46.12 g of solid. A small sample was recrystallized twice from water and once from ether-dichloroethane to give pure product, m.p. 187.5 -188.5° with decomposition (fast).

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturewas cooled
  3. extractionwas extracted with ether several times (total ether volume equals 1300 ml)
  4. dry with materialThe ether solution was dried (CaSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af2c059a674b4840afb27e57c30fb7c0
Source dataset
uspto-grants-1979_03
Patent number
US04144047

Reaction notes

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