Ethyl Acetate → HCID 59296155, compound

HRID 2233574Notes

Reaction equation

HRID 2233574 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10]Cl)[CH2:2][CH2:3][CH3:4].[Cl:22][C:23]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:24]=1[CH:25]=[O:26].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10][O:31][C:29]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[C:23]([Cl:22])[CH:30]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1853632-Chloro-4-hydroxybenzaldehydeHCID 230893954-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

Product 1

HCID 59296155HCID 59296155, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.2 g 4-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole and 1.5 g 2-Chloro-4-hydroxybenzaldehyde were dissolved in 150 ml dimethylformamide. 4.7 g cesiumcarbonate were added and the reaction mixture stirred at room temperature for four hours. The reaction mixture was then diluted by adding 300 ml ethyl acetate and washed three times with 50 ml water, saturated NaHCO3 solution and brine. The organic layer was dried over MgSO4 and the solvent removed in vacuo to provide 3.0 g 4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-benzaldehyde as oil.

Workup

  1. additionThe reaction mixture was then diluted
  2. washwashed three times with 50 ml water, saturated NaHCO3 solution and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b24806463b3c41ccbde33a7fc7d6320f
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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