Triethylamine → HCID 21097420, compound

HRID 747474Notes

Reaction equation

HRID 747474 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]([OH:9])[CH2:7][NH2:8])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19]>C(Cl)Cl>[CH2:1]([O:4][CH2:5][CH:6]([OH:9])[CH2:7][NH:8][C:17](=[O:21])[C:18]([CH3:20])=[CH2:19])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chloride2×HCID 980151-Amino-3-(2-propen-1-yloxy)-2-propanol

Product 1

HCID 21097420HCID 21097420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Allyloxy-2-hydroxy-propylamine made in Example 8 (110 g, 0.84 mol), triethylamine (85.6 g, 0.84 mol), and methylene chloride (300 mL) were mixed in a two-liter, two-neck flask, which was placed in an ice bath. To the above mixture, methacryloyl chloride (90.36 g, 84 mol) was added dropwise through an additional funnel at 0° C. After completion of the addition of methacryloyl chloride, the whole mixture was allowed to warm up to room temperature and stirred at ambient temperature overnight (˜15 hours). The reaction suspension was diluted with 250 mL of methylene chloride and washed with 5% aqueous sodium chloride solution, saturated aqueous sodium bicarbonate solution, 5% aqueous sodium chloride solution and then followed by washing with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulfate (100 g). After the removal of sodium sulfate by filtration, 4-methoxyphenol (0.5 g) was added to the filtrate. The solution was concentrated under vacuum using a rotovap to give about 122 g of crude N-(3-allyloxy-2-hydroxy-propyl)-2-methyl acrylamide. N-(3-Allyloxy-2-hydroxy-propyl)-2-methyl acrylamide was purified by distilling the raw material inhibited with 1% of 4-methoxyphenol under vacuum at 168° C.-170° C. (7-8 mbar) using Kugelrohr distillation equipment.

Workup

  1. additionwere mixed in a two-liter, two-neck flask, which
  2. customwas placed in an ice bath
  3. washwashed with 5% aqueous sodium chloride solution, saturated aqueous sodium bicarbonate solution, 5% aqueous sodium chloride solution
  4. washby washing with saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was dried over sodium sulfate (100 g)
  6. customAfter the removal of sodium sulfate
  7. filtrationby filtration, 4-methoxyphenol (0.5 g)
  8. additionwas added to the filtrate
  9. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-d1562aa146494b5bb7795c0c76aa4974
Source dataset
uspto-grants-2008_07
Patent number
US07396890B2

Reaction notes

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