Phosphoric Acid → N-(3-(Dimethylamino)-2,2-dimethylpropyl)acrylamide

HRID 1380698Notes

Reaction equation

HRID 1380698 reaction equation
[CH3:1][N:2]([CH3:9])[CH2:3][C:4]([CH3:8])([CH3:7])[CH2:5][NH2:6].P(=O)(O)(O)O.[C:15](O)(=[O:18])[CH:16]=[CH2:17]>C1(NC2C=CC3C(=CC=CC=3)C=2)C=CC=CC=1>[CH3:1][N:2]([CH3:9])[CH2:3][C:4]([CH3:8])([CH3:7])[CH2:5][NH:6][C:15](=[O:18])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 6581Acrylic AcidHCID 104477N,N,2,2-Tetramethylpropane-1,3-diamine

Product 1

HCID 88388N-(3-(Dimethylamino)-2,2-dimethylpropyl)acrylamideYield 67%

Reagents, catalysts & solvents 1

HCID 8679N-phenyl-2-naphthylamineCatalyst

Conditions

Temperature
200 °C

Procedure

A 500-ml three-neck flask fitted with a magnetic agitator, a thermometer, and a short column with a distillation set was charged with 260 g (2 mol) 3-dimethylamino-2,2-dimethylpropylamine; 4 g N-phenyl-β-naphthylamine; and 4 ml 85% phosphoric acid. 144 g (2 mol) acrylic acid was added drop by drop for 0.5 hours, whereupon the temperature of the mixture rose to 150° C. Finally, the mixture was heated to 200° C. in a nitrogen atmosphere for 2 hours, and then stirred at this temperature for 1 hour. During this time, 35.5 g of the distillate was obtained. Distillation was carried out in a vacuum after cooling and 247 g (67%) N-(3-dimethylamino-2,2-dimethylpropyl)acrylamide, boiling point 110°-115° C. at 66.5 Pa, was obtained.

Workup

  1. customA 500-ml three-neck flask fitted with a magnetic agitator
  2. customrose to 150° C
  3. customDuring this time, 35.5 g of the distillate was obtained
  4. distillationDistillation
  5. temperatureafter cooling

Sources & evidence

ORD record
ord-516838d7a5b84c41a0a4788aba6d3305
Source dataset
uspto-grants-1986_04
Patent number
US04582933

Reaction notes

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