Cesium carbonate → HCID 68278082, compound

HRID 1526917Notes

Reaction equation

HRID 1526917 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[CH:19]1([SH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH:19]1([S:25][CH2:2][C:3]2[N:4]=[C:5]([C:9]3[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=3)[O:6][C:7]=2[CH3:8])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 15290CyclohexanethiolHCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

Product 1

HCID 68278082HCID 68278082, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate (6.0 g, 22.64 mmol, 1.00 equiv), cyclohexanethiol (3.9 g, 33.62 mmol, 1.50 equiv) and cesium carbonate (11.1 g, 34.05 mmol, 1.50 equiv) in N,N-dimethylformamide (60 mL) was stirred under nitrogen overnight at 50° C. The reaction was then quenched by the addition of 30 mL of water. The precipitate was collected by filtration and washed with 3×10 mL of hexane to give 4.5 g (58%) of methyl 4-(4-(cyclohexylthiomethyl)-5-methyloxazol-2-yl)benzoate as a white solid after drying under vacuum.

Workup

  1. customThe reaction was then quenched by the addition of 30 mL of water
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with 3×10 mL of hexane

Sources & evidence

ORD record
ord-18fb47f37edf4d9795e6bd0fdf5b4010
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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