Dimethyl Sulfate → HCID 89620702, compound

HRID 1499997Notes

Reaction equation

HRID 1499997 reaction equation
[CH3:1][C:2]1[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[O:8][C:9]([CH3:12])=[N:10][N:11]=1)=[O:5].[C:25]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>CN(C=O)C>[CH3:25][N:6]([C:7]1[O:8][C:9]([CH3:12])=[N:10][N:11]=1)[C:4](=[O:5])[C:3]1[CH:13]=[CH:14][C:15]([C:21]([F:24])([F:23])[F:22])=[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 89620381HCID 89620381, compound

Product 1

HCID 89620702HCID 89620702, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

180 mg (0.495 mmol) of 2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methylsulfonyl)-4-(trifluoromethyl)benzamide are dissolved in 6 ml of DMF (abs.), and 68 mg (0.495 mmol) of K2CO3 and 0.047 ml (0.495 mmol) of dimethyl sulfate are added. The reaction mixture is boiled under reflux for 15 hours. Then the mixture is filtered, and the filtrate is concentrated and purified by column chromatography (silica gel; heptane/ethyl acetate).

Workup

  1. temperatureunder reflux for 15 hours
  2. filtrationThen the mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. custompurified by column chromatography (silica gel; heptane/ethyl acetate)

Sources & evidence

ORD record
ord-6c28bf76b3bf49b2b96d78a20d399b09
Source dataset
uspto-grants-2015_12
Patent number
US09204650B2

Reaction notes

Loading…