Acrylic Acid → N-Propylacetamide

HRID 968044

Reaction equation

HRID 968044 reaction equation
[C:1]([OH:5])(=O)[CH:2]=[CH2:3].C(N=C=[N:10][CH2:11][CH2:12][CH2:13]N(C)C)C.[NH2:17][C:18]([OH:24])([CH2:22][CH3:23])C(O)=O>O>[CH2:11]([NH:10][C:1](=[O:5])[CH3:2])[CH2:12][CH3:13].[CH2:1]([NH:17][C:18](=[O:24])[CH:22]=[CH2:23])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 6581Acrylic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 184611152-Amino-2-hydroxybutanoic acid

Product 2

HCID 21407N-PropylacetamideHCID 114794N-(n-Propyl) acrylamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Acrylic acid (20 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (30 g) were dissolved in water (300 mL). Then aminohydroxybutyric acid (2.0 g) was added to the obtained solution and reacted at room temperature for 10 hours. After the completion of the reaction, water was distilled off and the residue was sufficiently washed with hexane (200 mL) in 3 portions. Next, this residue was dissolved in dimethyl-formamide (350 mL), in which N-hydroxysuccinimide (3 g) and N,N′-dicyclohexylcarbodiimide (3 g) had been dissolved, and reacted overnight. After the completion of the reaction, the solvent was distilled off. Ethyl acetate was added to the residue thus obtained and the precipitate thus formed was filtered off. The filtrate was recovered and a fraction containing the target product was taken up by silica gel column chromatography with the use of ethyl acetate as a mobile phase and alumina column chromatography. Next, a half of the solvent was distilled off with an evaporator and recrystallization was carried out by adding a hexane solvent at −20° C. to thereby give the target monomers (N-propylacetamide, N-propyl acrylamide) (yield: 68%).

Workup

  1. customreacted at room temperature for 10 hours
  2. distillationwas distilled off
  3. washthe residue was sufficiently washed with hexane (200 mL) in 3 portions
  4. dissolutionNext, this residue was dissolved in dimethyl-formamide (350 mL), in which N-hydroxysuccinimide (3 g) and N,N′-dicyclohexylcarbodiimide (3 g)
  5. dissolutionhad been dissolved
  6. customreacted overnight
  7. customAfter the completion of the reaction
  8. distillationthe solvent was distilled off
  9. additionEthyl acetate was added to the residue
  10. customthus obtained
  11. customthe precipitate thus formed
  12. filtrationwas filtered off
  13. customThe filtrate was recovered
  14. additiona fraction containing the target product
  15. distillationNext, a half of the solvent was distilled off with an evaporator and recrystallization
  16. additionby adding a hexane solvent at −20° C.

Sources & evidence

ORD record
ord-33f6db3f89e74ea7acae4abe5a8385b0
Source dataset
uspto-grants-2005_10
Patent number
US06956077B1

Linked notes

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