Diethyl Sulfate → HCID 14801028, compound

HRID 728581Notes

Reaction equation

HRID 728581 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([CH3:16])=[O:15])[C:5]=1[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].S(OCC)(O[CH2:21][CH3:22])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([CH3:16])=[O:15])[C:5]=1[C:6]([O:8][CH2:21][CH3:22])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 14801027HCID 14801027, compound

Product 1

HCID 14801028HCID 14801028, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 4.0 g of 2-acetyl-6-acetaminobenzoic acid, 3.1 g of diethyl sulfate and 2.8 g of potassium carbonate in 40 ml of acetone was allowed to react under stirring under refluxing for 5 hours. After the reaction was over, the reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water and concentrated to obtain 4.1 g of ethyl 2-acetyl-6-acetaminobenzoate.

Workup

  1. customto react
  2. temperatureunder refluxing for 5 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b16c4f0d56ca444d9e421fed8f7cbea0
Source dataset
uspto-grants-1991_09
Patent number
US05049575

Reaction notes

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