Triethylamine → Propionamide propyl methacrylamide

HRID 968040Notes

Reaction equation

HRID 968040 reaction equation
Cl.N[CH2:3][CH2:4][CH2:5][CH:6]=[C:7]([CH3:11])[C:8]([NH2:10])=[O:9].C(OC(=O)CC)(=O)CC.C(N(CC)CC)C>CO>[C:8]([NH2:10])(=[O:9])[CH2:7][CH3:6].[CH2:5]([CH:6]=[C:7]([CH3:11])[C:8]([NH2:10])=[O:9])[CH2:4][CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31263Propionic anhydrideHCID 866009693-Aminopropyl methacrylamide hydrochloride

Product 1

HCID 86600968Propionamide propyl methacrylamideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.8 g of 3-aminopropyl methacrylamide hydrochloride was dissolved in a methanol solvent and 1.0 g of propionic anhydride and 0.9 g of triethylamine (TEA) were added thereto. The resultant mixture was stirred under ice-cooling for 4 hours. After the completion of the reaction, the solvent was distilled off with an evaporator and the precipitate was filtered off. The filtrate was recovered and introduced into a silica column. Thus, the eluate fraction containing the target product was taken up and subjected to recrystallization to thereby purify the target propionamide-propyl methacrylamide (yield: 95%). FIG. 2 shows the result of the mass spectrometry of the purified product while FIG. 3 shows the result of 1H-NMR thereof.

Workup

  1. additionwere added
  2. temperaturecooling for 4 hours
  3. customAfter the completion of the reaction
  4. distillationthe solvent was distilled off with an evaporator
  5. filtrationthe precipitate was filtered off
  6. customThe filtrate was recovered
  7. additionintroduced into a silica column
  8. additionThus, the eluate fraction containing the target product
  9. customsubjected to recrystallization

Sources & evidence

ORD record
ord-b22b9ba3f0b24ca0904a746381ae6e14
Source dataset
uspto-grants-2005_10
Patent number
US06956077B1

Reaction notes

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