Ethanol → Ethyl{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetate

HRID 460025

Reaction equation

HRID 460025 reaction equation
C([C:3](Br)([CH2:9][CH3:10])[C:4](=O)[C:5]([O-:7])=[O:6])C.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[S:19])=[CH:16][CH:15]=1.[CH2:25](O)[CH3:26]>>[CH3:10][C:9]1[N:20]=[C:18]([C:17]2[CH:21]=[CH:22][C:14]([C:13]([F:12])([F:23])[F:24])=[CH:15][CH:16]=2)[S:19][C:3]=1[CH2:4][C:5]([O:7][CH2:25][CH3:26])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 27348234-(Trifluoromethyl)thiobenzamideHCID 86592485Ethyl-3-bromooxopentanoate

Product 1

HCID 17972170Ethyl{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetate

Procedure

To a solution of ethyl-3-bromooxopentanoate (O. G. Kulinkovich e.t al., Synthesis, 1986, 378–379) (1.26 g) in absolute ethanol (6 ml) was added 4-(trifluoromethyl)thiobenzamide (1.24 g). The reaction was heated to reflux and stirred at this temperature for 18 hours under nitrogen. The mixture was then allowed to cool to room temperature, prior to cooling in ice. This resulted in crystallization of the product which was filtered and washed with ice cold ethanol to afford the title compound as beige crystals.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperatureto cooling in ice
  4. customThis resulted in crystallization of the product which
  5. filtrationwas filtered
  6. washwashed with ice cold ethanol

Sources & evidence

ORD record
ord-e23ffdeada3e44a3a7648acd82a300a3
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Linked notes

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