Dimethylamine → beta-Alanine, N,N-dimethyl-, ethyl ester

HRID 1075775Notes

Reaction equation

HRID 1075775 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]([O:8][CH2:9][CH3:10])(=[O:7])[CH:5]=[CH2:6].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.COC1C=CC(O)=CC=1>>[CH3:1][N:2]([CH2:6][CH2:5][C:4]([O:8][CH2:9][CH3:10])=[O:7])[CH3:3]

Participants

5

Reactant 4

HCID 674Dimethylamine2×HCID 7108PhenothiazineHCID 8821Ethyl Acrylate2×HCID 90154-Methoxyphenol

Product 1

HCID 88372beta-Alanine, N,N-dimethyl-, ethyl esterYield 97%

Conditions

Temperature
-13 °C

Procedure

To a chilled (-15°C.) reaction vessel there was added: anhydrous dimethylamine (100 grams); ethyl acrylate (250 grams); phenothiazine (0.5 gram); and p-methoxyphenol (0.5 gram). The mixture was maintained at -13°C. for 2 hours with stirring after which the temperature was allowed to rise to about 25°C. Unreacted dimethylamine and ethyl acrylate were removed by distillation. The product was recovered by distillation at 58°C. and 10 mm. mercury pressure in a yield of 97 percent. The product, designated herein as Amine Catalyst VIII, has the formula, (CH3)2NCH2CH2C(O)OC2H5, as verified analytically by infrared spectroscopy.

Workup

  1. temperatureTo a chilled
  2. custom(-15°C.) reaction vessel there
  3. additionwas added
  4. customto rise to about 25°C
  5. customwere removed by distillation
  6. distillationThe product was recovered by distillation at 58°C.

Sources & evidence

ORD record
ord-e9cfe0cee25a4215b30115aacaee16bb
Source dataset
uspto-grants-1976_05
Patent number
US03954749

Reaction notes

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