4-(Chloromethyl)benzoyl chloride → 4-(Chloromethyl)-N-hydroxybenzamide

HRID 1755873Notes

Reaction equation

HRID 1755873 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.Cl.[NH2:13][OH:14].C(=O)([O-])O.[Na+]>O.C(OCC)C>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:13][OH:14])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 158531224-(Chloromethyl)-N-hydroxybenzamideYield 91.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Chloromethyl-benzoyl chloride (18.9 g) (0.1 mol) and 13.8 g (0.2 mol) of hydroxylamine hydrochloride are suspended in 200 ml of water and 150 ml of diethyl ether. 25.2 g (0.3 mol) of sodium hydrogen carbonate are added while stirring. After 30 minutes the product is filtered off under suction and washed with water and diethyl ether. After drying in a high vacuum at room temperature there are obtained 17 g of white α-chloro-N-hydroxy-p-toluamide of m.p. 120°-145° C. (dec.).

Workup

  1. filtrationAfter 30 minutes the product is filtered off under suction
  2. washwashed with water and diethyl ether
  3. customAfter drying in a high vacuum at room temperature

Sources & evidence

ORD record
ord-7728eb3b50fd4bc99e926551f265cc82
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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