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

HRID 879133Notes

Reaction equation

HRID 879133 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-30344198a1b94ae7b2380611dbe9d09f
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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