1-Amino-2-propanol → N-(2-hydroxypropyl)methacrylamide

HRID 2166457Notes

Reaction equation

HRID 2166457 reaction equation
[NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].C([O-])([O-])=O.[K+].[K+].[CH3:12][C:13]([C:15](Cl)=[O:16])=[CH2:14]>C(#N)C.CO>[OH:5][CH:3]([CH3:4])[CH2:2][NH:1][C:15](=[O:16])[C:13]([CH3:14])=[CH2:12]

Participants

6

Reactant 3

HCID 41-Amino-2-propanolHCID 11430Potassium CarbonateHCID 13528Methacryloyl chloride

Product 1

HCID 38622N-(2-hydroxypropyl)methacrylamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Procedure

3.75 g of 1-amino-2-propanol (0.05 mol) were placed in a three-necked flask, equipped with dropping funnel and gas inlet and gas outlet pipe, together with 30 ml of acetonitrile (anhydrous) and 13.79 g of K2CO3 (0.1 mol), and cooled to 0° C. in an ice bath. 6.18 g of methacryl chloride (0.06 mol), dissolved in 30 ml of acetonitrile, were added dropwise over 30 minutes with constant stirring and gentle passage of nitrogen. After stirring for a further 60 minutes with ice cooling, the mixture was allowed to warm to room temperature and was stirred for a further 30 minutes. The batch was filtered through a glass frit and the precipitate was discarded. The filtrate was concentrated in a rotary evaporator until a viscous oil was produced. This was dissolved in 30 ml of methanol and separated from any precipitate which appeared. The filtrate was again concentrated in a rotary evaporator and the residual amounts of the solvent were removed in a high vacuum. The yield was 6.66 g.

Workup

  1. customequipped
  2. additionwere added dropwise over 30 minutes
  3. stirringAfter stirring for a further 60 minutes with ice cooling
  4. stirringwas stirred for a further 30 minutes
  5. filtrationThe batch was filtered through a glass frit
  6. concentrationThe filtrate was concentrated in a rotary evaporator until a viscous oil
  7. customwas produced
  8. customseparated from any precipitate which
  9. concentrationThe filtrate was again concentrated in a rotary evaporator
  10. customthe residual amounts of the solvent were removed in a high vacuum

Sources & evidence

ORD record
ord-300efb8abe87472781eb36315b842cc8
Source dataset
uspto-grants-1990_07
Patent number
US04945146

Reaction notes

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