Carbon Dioxide → Methyl[2-(phenylamino)ethyl]amine

HRID 1702492

Reaction equation

HRID 1702492 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][N:10]1[CH2:14][CH2:13]OC1=O.COCCOCCO.C(=O)=O>>[CH3:9][NH:10][CH2:14][CH2:13][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 8134Diethylene Glycol Monomethyl EtherHCID 8870Benzenamine hydrochloride (1:1)HCID 298312-Oxazolidinone, 3-methyl-

Product 1

HCID 10582940Methyl[2-(phenylamino)ethyl]amine

Conditions

Temperature
170 °C

Procedure

A mixture of aniline hydrochloride (13.0 g, 0.10 mole), 3-methyl-2-oxazolidinone (11.0 g, 0.109 mole) and 35 ml of 2-(2-methoxyethoxy)ethanol was heated to 170° C. in an oil bath. The reaction mixture became homogenous and carbon dioxide evolution occurred on heating. After 17 hours, the reaction was allowed to cool to room temperature. After a workup procedure similar to that described in Example 1 and distillation at 105° C. to 110° C. (0.4 mm), an 81 percent distilled yield of the product was obtained as a clear liquid. Product confirmation was made by the use of spectra evidence.

Workup

  1. temperatureon heating
  2. temperatureto cool to room temperature
  3. distillationAfter a workup procedure similar to that described in Example 1 and distillation at 105° C. to 110° C. (0.4 mm)
  4. distillationan 81 percent distilled yield of the product
  5. customwas obtained as a clear liquid

Sources & evidence

ORD record
ord-b4402926e87e4dc68f87a8052c946b9d
Source dataset
uspto-grants-1983_04
Patent number
US04381401

Linked notes

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