Water → HCID 54274887, compound

HRID 2287042Notes

Reaction equation

HRID 2287042 reaction equation
[CH3:1][C:2]([CH3:28])([CH:7]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[CH3:31]I.O>CN(C)C=O>[CH3:1][C:2]([CH3:28])([CH:7]([N:17]([CH3:31])[S:18]([C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)(=[O:19])=[O:20])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53810576HCID 53810576, compound

Product 1

HCID 54274887HCID 54274887, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 405 g of methyl 2,2-dimethyl-4-(p-methoxyphenyl)-3-(p-toluenesulphonamido)butyrate in 1800 ml of dry dimethylformamide is added to a mechanically stirred suspension of 52.8 g of sodium hydride in 320 ml of the same solvent. After the reaction mixture has been heated at 80° C. for 1 hour it is cooled when 93 ml of methyl iodide is added. After an additional period of heating (under reflux) the mixture, after being cooled, is poured into plenty of water. A white crystallisate separates. After filtration and drying it melts at 132°-134° C. Yield 96%.

Workup

  1. additionis added
  2. temperatureAfter an additional period of heating
  3. temperature(under reflux) the mixture
  4. temperatureafter being cooled
  5. filtrationAfter filtration
  6. customdrying it melts at 132°-134° C

Sources & evidence

ORD record
ord-04591f2b4924446385220f72640fb6b5
Source dataset
uspto-grants-1981_05
Patent number
US04268673

Reaction notes

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