Acetic Anhydride → N-(2-Acetoxyethyl)-N-methylaniline

HRID 2296871Notes

Reaction equation

HRID 2296871 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][OH:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([O:11][CH2:10][CH2:9][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 623402-(N-Methylanilino)ethanol

Product 1

HCID 12570555N-(2-Acetoxyethyl)-N-methylaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1 L flask was charged with 2-(N-methylanilino)ethanol (8) (151.3 g, 1 mole), methylene chloride (250 mL), and triethylamine (151 g, 1.48 mole). Acetic anhydride (153.35 g, 1.5 mole) was added to the solution at room temperature through an addition funnel. The product (7) was collected by vacuum distillation (122 g, bp 110° C. at 400 micron Hg).

Workup

  1. distillationThe product (7) was collected by vacuum distillation (122 g, bp 110° C. at 400 micron Hg)

Sources & evidence

ORD record
ord-8142dca0c87c48fd83449742c3c319fd
Source dataset
uspto-grants-2002_12
Patent number
US06489399B1

Reaction notes

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