Hydrochloric Acid → Ethyl 3,4-dichloro-1,2-thiazole-5-carboxylate

HRID 2163121Notes

Reaction equation

HRID 2163121 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([OH:10])=[O:9])[S:4][N:3]=1.Cl.O.C([O-])(O)=O.[Na+].[CH2:18](O)[CH3:19]>>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([O:10][CH2:18][CH3:19])=[O:9])[S:4][N:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 498373,4-Dichloro-5-isothiazolecarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 12889011Ethyl 3,4-dichloro-1,2-thiazole-5-carboxylateYield 83%

Procedure

3,4-Dichloro-5-isothiazolecarboxylic acid (55 g; 0.278 mol) was dissolved in 500 ml of ethanol. The solution was saturated with hydrochloric acid and then refluxed for 3 hrs. The ethanol was distilled on a rotary evaporator leaving a residue which was then charged into 200 ml of water and neutralized with NaHCO3. The water layer was extracted with 2x200 ml of Ch2CL2. The extracts were combined, dried over MgSO4, filtered and the solvent distilled. The remaining liquid was distilled to yield 52.3 g (83%) of ethyl 3,4-dichloroisothiazol-5-carboxylate by 92° (3.0 mm).

Workup

  1. temperaturerefluxed for 3 hrs
  2. distillationThe ethanol was distilled on a rotary evaporator
  3. customleaving a residue which
  4. extractionThe water layer was extracted with 2x200 ml of Ch2CL2
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. distillationthe solvent distilled
  8. distillationThe remaining liquid was distilled

Sources & evidence

ORD record
ord-fd1cbd05475343859a326d92b758269e
Source dataset
uspto-grants-1979_01
Patent number
US04132676

Reaction notes

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