3-Hydroxyacetanilide → HCID 19799805, compound

HRID 1460901Notes

Reaction equation

HRID 1460901 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].O[CH2:13][NH:14][C:15](=[O:18])[CH2:16][Cl:17]>Cl.CO>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:13][NH:14][C:15](=[O:18])[CH2:16][Cl:17])=[C:7]([OH:11])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 121243-HydroxyacetanilideHCID 62466N-Methylol-alpha-chloroacetamide

Product 1

HCID 19799805HCID 19799805, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 3-acetamidophenol (1.5 g, 10 mmol) and N-(hydroxymethyl)-2-chloroacetamide (1.2 g, 10 mmol) was stirred in 50 ml of 20% HCl in methanol at room temperature for 2 days. After removal of solvent, the desired product was isolated in 20% yield (0.51 g, 2 mmol) by chromatography (silica gel, eluted with ethyl acetate and hexane, 40/60).

Workup

  1. customAfter removal of solvent

Sources & evidence

ORD record
ord-66cc355a1fb845e7b7b7e7d8d546d253
Source dataset
uspto-grants-1991_12
Patent number
US05073173

Reaction notes

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