Cesium carbonate → HCID 69471232, compound

HRID 854552Notes

Reaction equation

HRID 854552 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:26]([O:28][C:29](=[O:40])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][C:33]=1[CH3:39])[CH3:27].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:26]([O:28][C:29](=[O:40])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38][CH2:2][C:3]2[S:7][C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)=[N:5][C:4]=2[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:34][C:33]=1[CH3:39])[CH3:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 16641178Ethyl (4-mercapto-2-methylphenoxy)acetateHCID 17951829HCID 17951829, compound

Product 1

HCID 69471232HCID 69471232, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-chloromethyl-4-phenethyl-2-(4-trifluoromethyl-phenyl)-thiazole (190 mg, 0.5 mmol) and (4-Mercapto-2-methyl-phenoxy)-acetic acid ethyl ester (100 mg, 0.44 mmol) in acetonitrile (3 mL) is added Cs2CO3 (325 mg, 1 mmol). The mixture is stirred at room temperature over night, quenched by water, extracted with ethyl acetate, dried over sodium sulfate. Column chromatography on silica gel of the crude product gave 210 mg (83.5% yield) of the title compound.

Workup

  1. customquenched by water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-adf78df12fbf4a578727f5b64c356f19
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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