Dimethylformamide → HCID 18613840, compound

HRID 1264938Notes

Reaction equation

HRID 1264938 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[S:3])[NH2:2].[F:14][C:15]([F:27])([F:26])[C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18](=O)[CH2:19]Br.CN(C)C=O>O>[F:14][C:15]([F:26])([F:27])[C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]1[N:2]=[C:1]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[S:3][CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27784302-Bromo-1-[2-(trifluoromethyl)phenyl]ethan-1-oneHCID 11401319Methyl 4-carbamothioylbenzoate

Product 1

HCID 18613840HCID 18613840, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of methyl 4-thiocarbamoylbenzoate (1.00 g), 2-trifluoromethyphenacyl bromide (1.50 g) and N,N-dimethylformamide (3 ml) was stirred at 120 to 130° C. for 3 hours. The reaction mixture was poured into water, and precipitated crystals were collected by filtration and then subjected to a silica gel column chromatography. From a fraction eluted with ethyl acetate-hexane (1:4, v/v), methyl 4-[4-(2-trifluoromethylphenyl)-2-thiazolyl]benzoate (1.01 g, yield: 54%) was obtained. The product was recrystallized from hexane-toluene to obtain colorless prisms. Melting point: 122 to 123° C.

Workup

  1. customprecipitated crystals
  2. filtrationwere collected by filtration
  3. washFrom a fraction eluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-4efe309de39241b4896d6681e585017c
Source dataset
uspto-grants-2003_04
Patent number
US06545009B1

Reaction notes

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