Diethylene Glycol Monomethyl Ether → HCID 10703579, compound

HRID 1702494Notes

Reaction equation

HRID 1702494 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([N:14]1[CH2:18][CH2:17]OC1=O)([O:11][CH2:12][CH3:13])=[O:10].COCCOCCO>>[CH2:12]([O:11][C:9](=[O:10])[NH:14][CH2:18][CH2:17][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:13]

Participants

4

Reactant 3

HCID 8134Diethylene Glycol Monomethyl EtherHCID 8870Benzenamine hydrochloride (1:1)HCID 12292572HCID 12292572, compound

Product 1

HCID 10703579HCID 10703579, compoundYield 26%

Conditions

Temperature
160 °C

Procedure

A mixture of aniline hydrochloride (8.7 g, 66.9 mmole), N-carboethoxy-2-oxazolidinone (10.1 g, 63.5 mmole) and 25 ml of 2-(2-methoxyethoxy)ethanol was heated to 160° C. Gas evolution began occurring at 140° C. and continued for 3 hours. The dark homogenous reaction solution was allowed to cool to ambient temperature and worked up according to the procedure described in Example 1. Distillation at 170° C. (0.5 mm) gave a 26 percent yield of a clear oil which slowly solidified on standing.

Workup

  1. custombegan occurring at 140° C.
  2. temperatureto cool to ambient temperature
  3. distillationDistillation at 170° C. (0.5 mm)

Sources & evidence

ORD record
ord-a99b8cc5ee7c455b9c2e1f1f7ebbeed6
Source dataset
uspto-grants-1983_04
Patent number
US04381401

Reaction notes

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