Sulfite → N-(4-Methoxyphenyl)Acetamide

HRID 1262737Notes

Reaction equation

HRID 1262737 reaction equation
S([O-])([O-])=O.[C:5](=[O:8])([O-])[O-].[K+].[K+].[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18](O)=[CH:17][CH:16]=1)(=[O:13])[CH3:12]>CN(C)C=O>[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:8][CH3:5])=[CH:17][CH:16]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 1099SulfiteHCID 1983AcetaminophenHCID 11430Potassium Carbonate

Product 1

HCID 5827N-(4-Methoxyphenyl)AcetamideYield 138.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a three-necked 100 ml flask equipped for reflux and fitted with a mechanical stirrer was added 10 ml (0.12 mol) of diemthyl sulfite, 2.0 g (0.014 mol) of potassium carbonate, 10 ml dimethylformamide and 5.0 g (0.033 mol) of p-acetamidophenol. The mixture was heated to 100° C. for six hours then quenched while hot with 200 ml of water. The solution was made basic with dilute caustic and the organic materials were extracted into methylene chloride. The extracts were concentrated in vacuo to give 3.2 g of p-acetamidoanisole.

Workup

  1. customTo a three-necked 100 ml flask equipped
  2. temperaturefor reflux
  3. customfitted with a mechanical stirrer
  4. customthen quenched while hot with 200 ml of water
  5. additionwith dilute caustic
  6. extractionthe organic materials were extracted into methylene chloride
  7. concentrationThe extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-be4a78b376c1401ea975d481a20f2b84
Source dataset
uspto-grants-1984_06
Patent number
US04453018

Reaction notes

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