Iodoacetamide → 2-(2-Nitrophenoxy)acetamide

HRID 863248Notes

Reaction equation

HRID 863248 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][C:9]([NH2:11])=[O:10].[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])([O-:14])=[O:13]>CC(C)=O>[C:9]([CH2:8][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N+:12]([O-:14])=[O:13])(=[O:10])[NH2:11]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 69472-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 49318272-(2-Nitrophenoxy)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8.0 g of potassium carbonate and 11.4 g of iodoacetamide are added to a solution of 4.0 g of 2-nitrophenol in 50 ml acetone. The reaction mixture is heated under reflux for 7 h and then concentrated. The residue is dissolved in chloroform and extracted with 0.05N of sodium hydroxide solution. Recyrstallization of the crude product from tetrahydrofuran gives 2-(carbamoylmethoxy)nitrobenzene of mp 190°-1° C.; Rf (O)=0.55.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 7 h
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in chloroform
  5. extractionextracted with 0.05N of sodium hydroxide solution

Sources & evidence

ORD record
ord-3dc3f48d9b5549fc99e00f009cf9de65
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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