Sulfuric Acid → N-(1,1-dimethyl-3-dimethylaminopropyl)acrylamide

HRID 267484Notes

Reaction equation

HRID 267484 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].S(=O)(=O)(O)O.[CH3:10][N:11]([CH3:17])[CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15].C(C1C([OH:28])=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[OH-].[Na+]>O>[CH3:15][C:14]([NH:4][C:1](=[O:28])[CH:2]=[CH2:3])([CH3:16])[CH2:13][CH2:12][N:11]([CH3:17])[CH3:10]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 52599752-Buten-1-amine, N,N,3-trimethyl-

Product 1

HCID 1639462N-(1,1-dimethyl-3-dimethylaminopropyl)acrylamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A resin flask is cooled to 0° C. and 450 grams (8.5 moles) of acrylonitrile, 1020 grams (10 moles) of sulfuric acid and 37 grams of water are added. To this mixture are then added 475 grams (4.2 moles) of the 1-dimethylamino-3-methyl-2-butene prepared as described above, and 8.5 grams of 2,6-di-t-butyl-p-cresol. The mixture is stirred at 68° C. for about 1 hour and is then neutralized with about 30% sodium hydroxide. The organic layer is separated, diluted with 2050 ml. of methanol and neutralized with ammonia. An additional 1000 ml. of methanol is added and the solution is filtered. The methanol is stripped from the filtrate and the residue is distilled. There is obtained 400 grams (64.5% of the theoretical amount) of the desired N-(1,1-dimethyl-3-dimethylaminopropyl)acrylamide boiling at 75°-92° C./0.25-0.9 mm. The nitrogen analysis is 15.4%, as compared with a theoretical value of 15.2%.

Workup

  1. customprepared
  2. customThe organic layer is separated
  3. additiondiluted with 2050 ml
  4. additionof methanol is added
  5. filtrationthe solution is filtered
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-e12ee3a14c334806b57a51ab2aee0df8
Source dataset
uspto-grants-1976_03
Patent number
US03943114

Reaction notes

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