Ethanol → Ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylate

HRID 1920237Notes

Reaction equation

HRID 1920237 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](=[S:6])[NH2:5].C([CH:14](Br)[C:15](=O)[C:16]([O-:18])=[O:17])C.[CH2:21](O)[CH3:22]>>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]1[S:6][CH:14]=[C:15]([C:16]([O:18][CH2:21][CH3:22])=[O:17])[N:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 126832122,6-Difluorobenzene-1-carbothioamideHCID 21948992Ethylbromopyruvate

Product 1

HCID 59455697Ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylateYield 84%

Procedure

A solution of 2,6-difluorobenzothioamide (1.0 eq) and ethylbromopyruvate (1.0 eq.) in ethanol (1.0 M) was heated in the microwave at 130° C. for 30 minutes. Upon removal of volatiles in vacuo, ethyl acetate was added and the solution was washed with Na2CO3(sat.), with NaCl(sat.), was dried over MgSO4, filtered and concentrated yielding ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylate (84%). LCMS (m/z): 270.1 (MH+); LC Rt=3.79 min.

Workup

  1. customUpon removal of volatiles in vacuo, ethyl acetate
  2. additionwas added
  3. washthe solution was washed with Na2CO3(sat.), with NaCl(sat.)
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5913f3fb4eb842b4b8f20c63978760a0
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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