Potassium Hydroxide → HCID 22282483, compound

HRID 1062674Notes

Reaction equation

HRID 1062674 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:15]([O:17]CC)=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[CH:8]=2)[N:6]=1.[OH-].[K+]>CO.O>[Cl:1][C:2]1[S:3][C:4]([C:15]([OH:17])=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[CH:8]=2)[N:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22282476HCID 22282476, compound

Product 1

HCID 22282483HCID 22282483, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of of 2-chloro-4-(3-cyanophenyl)-5-carboethoxythiazole (0.44 g, 1.45 mmol) in 25 mL of methanol and 25 mL of water was added potassium hydroxide (0.09 g, 1.6 mmol). The resulting solution was stirred at reflux for 2 h and then was cooled to room temperature. The methanol was removed in vacuo and the aqueous layer was diluted with water and washed with hexanes. The hexane layer was discarded. The aqueous layer was acidified and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (MgSO4) and concentrated to yield 0.33 g (97%) of the title compound which was used without further purification. MS (ESI)−262.9 (M−H)−.

Workup

  1. temperatureat reflux for 2 h
  2. customThe methanol was removed in vacuo
  3. additionthe aqueous layer was diluted with water
  4. washwashed with hexanes
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a464b7f918d1438a81301ae8b7559c48
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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