Hydrochloric Acid → 3-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-Xylyl)-4,5-Isothiazoledicarboxylic Acid

HRID 1448680Notes

Reaction equation

HRID 1448680 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([C:13]2[C:17]([C:18]([O:20]C)=[O:19])=[C:16]([C:22]([O:24]C)=[O:23])[S:15][N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Na+].Cl>O>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2[C:17]([C:18]([OH:20])=[O:19])=[C:16]([C:22]([OH:24])=[O:23])[S:15][N:14]=2)[CH:4]=[C:3]([C:2]([F:1])([F:27])[F:26])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12437420Dimethyl 3-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-Xylyl)-4,5-Isothiazoledicarboxylate

Product 1

HCID 124374403-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-Xylyl)-4,5-Isothiazoledicarboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.7 g (0.0356 mol) of dimethyl 3-(α,α,α,α',α',α'-hexafluoro-3,5-xylyl)-4,5-isothiazoledicarboxylate, 7.2 g (0.18 mol) of NaOH, and 45 ml of water was held at reflux for 2 hours, was cooled, extracted twice with ether, and acidified with 30 ml (0.36 mol) of concentrated HCl. The resultant mixture was extracted three times with ether; these ether extracts were combined, dried (CaSO4), and concentrated under vacuum to 12.8 g (93.4%) of white solid, m.p. 193°-193.5° with decomposition.

Workup

  1. temperatureat reflux for 2 hours
  2. temperaturewas cooled
  3. extractionextracted twice with ether
  4. extractionThe resultant mixture was extracted three times with ether
  5. dry with materialdried (CaSO4)
  6. concentrationconcentrated under vacuum to 12.8 g (93.4%) of white solid, m.p. 193°-193.5° with decomposition

Sources & evidence

ORD record
ord-759d32389f24490da30ec222cc17015d
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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