Benzenamine hydrochloride (1:1) → HCID 19841690, compound

HRID 1702493Notes

Reaction equation

HRID 1702493 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15]OC1=O>COCCOCCO>[OH:9][CH2:10][CH2:11][NH:12][CH2:16][CH2:15][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 8870Benzenamine hydrochloride (1:1)HCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-

Product 1

HCID 19841690HCID 19841690, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Conditions

Temperature
168 °C

Procedure

A mixture of aniline hydrochloride (19.5 g, 0.15 mole), 3-(2-hydroxyethyl)-2-oxazolidinone (20.6 g, 0.157 mole) and 50 ml of 2-(2-methoxyethoxy)ethanol was heated to 168° C. for 16 hours. The orange solution was cooled to room temperature and worked up in a procedure similar to that cited in Example 1. Kugelrohr distillation at 150° C. to 160° C. (0.2 to 0.3 mm) gave a 67 percent yield of the material as a pale yellow oil. Spectral evidence confirmed its structure.

Workup

  1. temperatureThe orange solution was cooled to room temperature
  2. distillationKugelrohr distillation at 150° C. to 160° C. (0.2 to 0.3 mm)

Sources & evidence

ORD record
ord-6af4692bb15e42b995c10b99d14c2456
Source dataset
uspto-grants-1983_04
Patent number
US04381401

Reaction notes

Loading…