Water → N-(4-Fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamide

HRID 1781110Notes

Reaction equation

HRID 1781110 reaction equation
Cl[CH2:2][C:3]([N:5]([CH:13]([CH3:15])[CH3:14])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:4].C(=O)([O-])[O-:17].[Na+].[Na+].O>CN1CCCC1=O>[OH:17][CH2:2][C:3]([N:5]([CH:13]([CH3:15])[CH3:14])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 109662942-Chloro-N-(4-fluorophenyl)-N-(1-methylethyl)acetamide

Product 1

HCID 6452934N-(4-Fluorophenyl)-2-hydroxy-N-(1-methylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a suitable apparatus (500 ml flask), 23.0 g (0.1 mol) of N-chloroacetyl-N-isopropyl-4-fluoroaniline and 11.7 g (0.11 mol) of sodium carbonate are refluxed (100° C.) in a solution of 140 ml of water and 200 ml of N-methylpyrrolidone. After 2.5 hours, the solvent mixture is stripped off in vacuo and the residue distilled at 2 to 3 torr and 132° to 135° C. This gives 18.1 g (86% of theory) of N-hydroxyacetyl-N-isopropyl-(4-fluoroaniline) with a purity of 99.1% (GC).

Workup

  1. distillationthe residue distilled at 2 to 3 torr and 132° to 135° C

Sources & evidence

ORD record
ord-ce568f1ccd5b44b58402f591866b07a9
Source dataset
uspto-grants-1997_05
Patent number
US05631403

Reaction notes

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