Water → N-(2-Chloro-4-formylphenyl)acetamide

HRID 1168148Notes

Reaction equation

HRID 1168148 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Cl:13][O-].[Na+].O>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 739424-AcetamidobenzaldehydeHCID 23665760Sodium Hypochlorite

Product 1

HCID 22991945N-(2-Chloro-4-formylphenyl)acetamideYield 32%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6.43 g (0.039 mole) 4-acetamidobenzaldehyde (14) (Aldrich, A180-0) in 55 mL of glacial acetic acid, was added 100 mL of 5.25% solution of sodium hypochlorite (Clorox, Pathmark brand) and the reaction mixture was stirred at room temperature for 48 hours. A white precipitate developed in the reaction mixture when a sample of the reaction mixture was taken off for TLC. The mixture was poured into 100 mL water and filtered to give 2.5 g (32%) of 24 as white powder, mp 110-113°. Infrared (IR) and NMR analysis gave the following results:

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-731a09dfc09f43dd89c3a42f47a5d0a4
Source dataset
uspto-grants-2003_09
Patent number
US06624153B2

Reaction notes

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