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Potassium Carbonate → N-(2,3-Dihydroxypropyl)-2-methylprop-2-enamide

HRID 2253564
Notes
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Reaction equation

HRID 2253564 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].C([O-])([O-])=O.[K+].[K+].[C:13](Cl)(=[O:17])[C:14]([CH3:16])=[CH2:15]>CN(C)C=O>[OH:6][CH:3]([CH2:4][OH:5])[CH2:2][NH:1][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13528Methacryloyl chlorideHCID 735613-Amino-1,2-propanediol

Product 1

HCID 18783193N-(2,3-Dihydroxypropyl)-2-methylprop-2-enamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

4.65 g of 3-amino-1,2-propanediol (0.05 mol) were dissolved in 30 ml of dimethylformamide (anhydrous). This solution and 13.8 g of K2CO3 were placed in a 100 ml three-necked flask with dropping funnel and gas inlet and gas outlet tubes. The mixture was cooled to 0° C. in an ice bath. While stirring gently and slowly bubbling nitrogen through, 6.18 ml of methacryloyl chloride (0.06 mol) dissolved in 30 ml of dimethylformamide were added dropwise over the course of 30 minutes. The mixture was stirred, while cooling in ice, for a further hour and then allowed to warm to room temperature and was stirred for a further 30 minutes. The reaction mixture was filtered through a fluted filter, and the residue was discarded. The filtrate was concentrated to a viscous oil in a rotary evaporator. This oil was dissolved in 30 ml of methanol, a second filtration was carried out, and the filtrate was again concentrated in a rotary evaporator. The residues of the solvent were removed under high vacuum. The yield was 8.52 g.

Workup

  1. additionwere added dropwise over the course of 30 minutes
  2. stirringThe mixture was stirred
  3. temperaturewhile cooling in ice, for a further hour
  4. temperatureto warm to room temperature
  5. stirringwas stirred for a further 30 minutes
  6. filtrationThe reaction mixture was filtered through
  7. filtrationa fluted filter
  8. concentrationThe filtrate was concentrated to a viscous oil in a rotary evaporator
  9. dissolutionThis oil was dissolved in 30 ml of methanol
  10. filtrationa second filtration
  11. concentrationthe filtrate was again concentrated in a rotary evaporator
  12. customThe residues of the solvent were removed under high vacuum

Sources & evidence

ORD record
ord-4d1acf79a9eb40ab9af9d80a3843bfb1
Source dataset
uspto-grants-1993_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05232859

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes