Ethyl Acetate → HCID 59296133, compound

HRID 2233552Notes

Reaction equation

HRID 2233552 reaction equation
[F:1][S:2]([F:15])([F:14])([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.[CH3:16][O:17][C:18](=[O:25])[CH2:19][C:20](=O)[CH:21](Br)[CH3:22].[CH2:26](OC(=O)C)C>CC(C)=O>[CH2:16]([O:17][C:18](=[O:25])[CH2:19][C:20]1[N:9]=[C:7]([C:6]2[CH:5]=[CH:4][C:3]([S:2]([F:12])([F:13])([F:14])([F:15])[F:1])=[CH:11][CH:10]=2)[S:8][C:21]=1[CH3:22])[CH3:26]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 59296136(OC-6-21)-[4-(Aminothioxomethyl)phenyl]pentafluorosulfur

Product 1

HCID 59296133HCID 59296133, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0 g 4-Pentafluorosulfanyl-thiobenzamide and 9.93 g 4-bromo-3-oxo-pentanoic acid methyl ester were dissolved in 30 ml acetone and refluxed for one hour. The cooled reaction mixture was diluted by adding 250 ml ethylacetate and washed three times with saturated NaHCO3 solution. The organic layer was dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography with the eluent n-heptane:ethyl acetate=5:1 to provide 4.5 g [5-Methyl-2-(4-pentafluorosulfanyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester as an oil which solidified upon standing.

Workup

  1. temperaturerefluxed for one hour
  2. customThe cooled reaction mixture
  3. additionwas diluted
  4. washwashed three times with saturated NaHCO3 solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography with the eluent n-heptane

Sources & evidence

ORD record
ord-700f0d0a9bcb4b5783a2c32746f10ecd
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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