Acetic Anhydride → N-(hydroxymethyl)acetamide acetate

HRID 654131Notes

Reaction equation

HRID 654131 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-7855edfd6e3d4795bd89ba4395522031
Source dataset
uspto-grants-1992_07
Patent number
US05130328

Reaction notes

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