Dimethyl Sulfate → HCID 86703403, compound

HRID 1522944Notes

Reaction equation

HRID 1522944 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:5]([F:19])=[C:6]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1.S(OC)(O[CH3:24])(=O)=O>C1(C)C=CC=CC=1>[Cl:3][C:4]1[C:5]([F:19])=[C:6]([N:10]([CH3:24])[C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 26897410HCID 26897410, compound

Product 1

HCID 86703403HCID 86703403, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into toluene (60 g) were added 85% potassium hydroxide (2.8 g, 0.05 mol) and 10.0 g (0.40 mol) of N-(3-chloro-2-fluorophenyl)benzamide obtained above. While the reaction mixture was heated at reflux, 6.1 g (0.05 mol) of dimethyl sulfate was added dropwise. The reaction was conducted with a dean stark trap to remove the water generated. After the dropwise addition was completed, the mixture was stirred for 1 hour and allowed to cool to room temperature. The resultant was mixed with 20 g of a 5% aqueous sodium hydroxide solution and stirred for 1 hour. The mixture was allowed to separate to give a toluene layer, which was washed with 40 g of water. The toluene layer was concentrated under reduced pressure, and the resultant residue was washed with n-hexane to obtain 9.97 g of the title compound (yield: 94%) as a white solid.

Workup

  1. customobtained above
  2. temperatureWhile the reaction mixture was heated
  3. temperatureat reflux
  4. customThe reaction was conducted with a dean stark trap
  5. customto remove the water
  6. additionAfter the dropwise addition
  7. additionThe resultant was mixed with 20 g of a 5% aqueous sodium hydroxide solution
  8. stirringstirred for 1 hour
  9. customto separate
  10. customto give a toluene layer, which
  11. washwas washed with 40 g of water
  12. concentrationThe toluene layer was concentrated under reduced pressure
  13. washthe resultant residue was washed with n-hexane

Sources & evidence

ORD record
ord-5b6e70eb19954bd4a9b00dedf8205601
Source dataset
uspto-grants-2015_07
Patent number
US09079827B2

Reaction notes

Loading…