Triethylamine → HCID 58542500, compound

HRID 1843104Notes

Reaction equation

HRID 1843104 reaction equation
[F:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[C:3](=[S:5])[NH2:4].Cl[CH:12]([C:18](=O)[C:19]([F:22])([F:21])[F:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14].FF.C(N(CC)CC)C>C(#N)C>[F:1][C:2]([F:10])([C:3]1[S:5][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]([C:19]([F:20])([F:22])[F:21])[N:4]=1)[C:6]([F:9])([F:8])[F:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24524FluorineHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoateHCID 20086735HCID 20086735, compound

Product 1

HCID 58542500HCID 58542500, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

557 mg (3.10 mmol) of 2,2,3,3,3-pentafluoropropanethioamide and 746 mg (3.41 mmol) of ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate (commercially available or can be prepared in accordance with Journal of Fluorine Chemistry 2004, 125, 1287-1290) are dissolved in 15 ml of acetonitrile, and 0.86 ml (6.19 mmol) of triethylamine is added dropwise. The reaction mixture is heated at reflux for 5 hours and then left at room temperature for two days. Chromatographic purification on silica gel gives 568 mg of ethyl 2-(pentafluoroethyl)-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate (13%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 5 hours
  3. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-a154f0f74afd4f8396b433bc20ca80fa
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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