2-Oxazolidinone → 36271-21-3

HRID 1702491Notes

Reaction equation

HRID 1702491 reaction equation
[ClH:1].[CH3:2][NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O1[CH2:14][CH2:13][NH:12]C1=O>COCCOCCO>[ClH:1].[CH3:2][N:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:14][CH2:13][NH2:12]

Participants

4

Reactant 2

HCID 739492-OxazolidinoneHCID 12206974N-Methylanilinium chloride

Product 1

HCID 2272314436271-21-3

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

In a procedure similar to Example 1, N-methylaniline hydrochloride (17.4 g, 0.10 mole), 2-oxazolidinone (8.7 g, 0.10 mole) and 50 ml of 2-(2-methoxyethoxy)-ethanol were heated for four hours. Removal of the solvent in vacuo gave a quantitative yield of N-methyl-N-phenyl-1,2-ethanediamine hydrochloride as a purplish solid. Workup as before afforded the crude diamine in also a quantitative crude yield as a dark yellow liquid. Distillation at 95° C. to 100° C. (0.5 mm Hg) gave a 79 percent yield of the purified product as a clear liquid. Spectral data and gas chromatographic analysis as compared to an authentic sample confirmed its structure.

Workup

  1. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-c833d5e15a244ba1a98a69f0fb1ddb6d
Source dataset
uspto-grants-1983_04
Patent number
US04381401

Reaction notes

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