Carbon Dioxide → N-[3-(Dimethylamino)-1,1-dimethylbutyl]-2-propenamide

HRID 267483Notes

Reaction equation

HRID 267483 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:16])[CH2:12][CH2:13]OC)([CH3:9])[CH2:3][CH:4]([N:6]([CH3:8])[CH3:7])[CH3:5].[OH-].[Na+].C1(C=CC(O)=CC=1)O.C(=O)=O>>[CH3:9][C:2]([NH:10][C:11](=[O:16])[CH:12]=[CH2:13])([CH3:1])[CH2:3][CH:4]([N:6]([CH3:8])[CH3:7])[CH3:5]

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 785HydroquinoneHCID 14798Sodium HydroxideHCID 21514639HCID 21514639, compound

Product 1

HCID 20432749N-[3-(Dimethylamino)-1,1-dimethylbutyl]-2-propenamide

Conditions

Temperature
80 °C

Procedure

A mixture of 144.7 parts (0.63 mole) of N-(1,1-dimethyl-3-dimethylaminobutyl)-3-methoxypropionamide, 1 part of solid sodium hydroxide and 1 part of hydroquinone is charged to a reaction flask fitted with a condenser with a Dry Ice-cooled receiver, a stirrer and temperature control means. The pressure in the flask is reduced to less than 5 mm. and the flask is heated to 80° C. Vigorous reaction begins and liquid condenses in the receiver. After about one-half hour, the temperature is increased to 90° C. and this temperature is maintained for 3 hours. The product is distilled and the desired N-(1,1-dimethyl-3-dimethylaminobutyl)acrylamide is obtained at 80°-91° C./0.3-0.4 mm. The yield is 109.1 parts, or 87.4% of the theoretical amount, and the nitrogen percentage is the calculated 14.1%.

Workup

  1. additionis charged to a reaction flask
  2. temperaturecooled receiver, a stirrer and temperature control
  3. customVigorous reaction
  4. waitAfter about one-half hour
  5. temperaturethe temperature is increased to 90° C.
  6. temperaturethis temperature is maintained for 3 hours
  7. distillationThe product is distilled

Sources & evidence

ORD record
ord-bbbdcf249d1348b1a927a198314ea3ff
Source dataset
uspto-grants-1976_03
Patent number
US03943114

Reaction notes

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