Ethylene Oxide → 4-acetamino-3-methyl-N-(beta-hydroxyethyl)-N-ethylaniline

HRID 436549

Reaction equation

HRID 436549 reaction equation
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([NH:9][CH2:10][CH3:11])=[CH:7][C:6]=1[CH3:14])[C:2]([CH3:4])=[O:3].[CH2:15]1[O:17][CH2:16]1>C(O)C>[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([N:9]([CH2:15][CH2:16][OH:17])[CH2:10][CH3:11])=[CH:7][C:6]=1[CH3:14])[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 2

HCID 6354Ethylene OxideHCID 214528314-Acetamino-3-methyl-N-ethylaniline

Product 1

HCID 214528374-acetamino-3-methyl-N-(beta-hydroxyethyl)-N-ethylaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.2g (0.08 mole) of 4-acetamino-3-methyl-N-ethylaniline obtained in Example 1, Part C, 4.2g (0.09 mole) of ethylene oxide and 50ml of ethanol were fed into an autoclave and reacted for 1 hour at 120° to 130° C in the closed autoclave. Thereafter, ethanol was distilled off to obtain crystals of 4-acetamino-3-methyl-N-(β-hydroxyethyl)-N-ethylaniline. The crystals were recrystallized from ethyl acetate to obtain 18.5g of white crystals.

Workup

  1. customreacted for 1 hour at 120° to 130° C in the closed autoclave
  2. distillationThereafter, ethanol was distilled off

Sources & evidence

ORD record
ord-f605f6d338414cef8d67e0b2cef64a81
Source dataset
uspto-grants-1977_02
Patent number
US04009205

Linked notes

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