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Ethyl 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylate → 2-(2,2,2-Trifluoroethyl)-1,3-thiazole-4-carboxylic acid

HRID 471142
Notes
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Reaction equation

HRID 471142 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]([O:11]CC)=[O:10])[N:8]=1>Cl.O>[F:15][C:2]([F:1])([F:14])[CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9]([OH:11])=[O:10])[N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 57989344Ethyl 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylate

Product 1

HCID 579889492-(2,2,2-Trifluoroethyl)-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2-(2,2,2-trifluoroethyl)thiazole-4-carboxylate (example 67, step c) (0.3 g) in concentrated hydrochloric acid (7 mL) and water (7 mL) was heated at 80° C. for 5 hours under nitrogen. The solvent was evaporated under a stream of nitrogen and the residue partitioned between ethyl acetate (40 mL) and brine (3 mL). The organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.23 g.

Workup

  1. customThe solvent was evaporated under a stream of nitrogen
  2. customthe residue partitioned between ethyl acetate (40 mL) and brine (3 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-3ad11f1093ed4264bb13410edb2826a8
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08629271B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes