2-Bromo-1,1-dimethoxyethane → 2-(4-(Trifluoromethyl)phenyl)thiazole

HRID 1460995

Reaction equation

HRID 1460995 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](=[S:9])[NH2:8])=[CH:5][CH:4]=1.CO[CH:16](OC)[CH2:17]Br>Cl.C(O)C>[F:13][C:2]([F:12])([F:1])[C:3]1[CH:11]=[CH:10][C:6]([C:7]2[S:9][CH:16]=[CH:17][N:8]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 27348234-(Trifluoromethyl)thiobenzamide

Product 1

HCID 146019692-(4-(Trifluoromethyl)phenyl)thiazoleYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of 5.0 grams (0.024 mole) of 4-trifluoromethylbenzthioamide, 4.4 grams (0.026 mole) of bromoacetaldehyde dimethyl acetal, and 4 drops of concentrated hydrochloric acid in 50 ml of ethanol was heated at reflux for 18 hours. After this time the reaction mixture was subjected to column chromatography on silica gel. Elution was accomplished using 20% ethyl acetate in hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 3.3 grams of 2-(4-trifluoromethylphenyl)thiazole. The nmr spectrum was consistent with the proposed structure. The reaction was repeated several times.

Workup

  1. temperatureat reflux for 18 hours
  2. washElution
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52935fdb1b064cff904a505076b8fd46
Source dataset
uspto-grants-1991_12
Patent number
US05073564

Linked notes

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