Acetic Anhydride → N-(hydroxymethyl)acetamide acetate

HRID 129623Notes

Reaction equation

HRID 129623 reaction equation
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].[OH:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12]>N1C=CC=CC=1>[C:1]([OH:4])(=[O:3])[CH3:2].[OH:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69365Formicin

Product 1

HCID 86745977N-(hydroxymethyl)acetamide acetateYield 900%

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

Acetic anhydride (25 g) and pyridine (10 drops) is added to N-(hydroxymethyl)acetamide (9 g, 0.1 mol). The reaction mixture is stirred overnight at room temperature, concentrated in vacuo and chased with xylene to give the title product as an oil (11.9 g, 0.9 mol) which is identified by 1HNMR spectral analysis.

Workup

  1. concentrationconcentrated in vacuo and chased with xylene

Sources & evidence

ORD record
ord-7c0bd3edec95447594664c9e2887776d
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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