Acryloyl chloride → HCID 23132167, compound

HRID 1437760Notes

Reaction equation

HRID 1437760 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]([OH:8])[CH3:7])[CH2:2][CH3:3].[OH-:9].[Na+].[C:11](Cl)(=[O:14])[CH:12]=[CH2:13]>C(Cl)(Cl)Cl>[C:1]([N:4]([CH2:5][CH:6]([OH:8])[CH2:7][N:4]([CH2:1][CH2:2][CH3:3])[C:11](=[O:14])[CH:12]=[CH2:13])[CH2:5][CH2:6][CH3:7])(=[O:9])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 3806320HCID 3806320, compound

Product 1

HCID 23132167HCID 23132167, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

17.43 g (0.100 mol) of 1,3-bis-(propylamino-propan-2-ol was mixed with 110 ml (0.220 mol) of 2N caustic soda solution and stirred at room temperature for 10 minutes. The mixture was cooled to 0° C. A solution of 19.46 g (0.215 mol) of acrylic acid chloride and 20 mg of BHT in 120 ml of chloroform was added dropwise at 0° C. within 3 hours 30 minutes. After the addition was completed the reaction mixture was stirred at 0° C. for 2 hours 30 minutes. Organic and aqueous phases were separated. The aqueous phase was saturated with NaCl and extracted with 5×80 ml of methylene chloride. The combined organic phases were dried over Na2SO4, filtered, concentrated in a rotary evaporator after addition of 20 mg of BHT and dried in a fine vacuum. The raw product was purified by means of two-fold column chromatography (silica gel 60, 0.035-0.070 mm, ethyl acetate). 11.92 g (42.2 mmol; 42%) of the pure product was obtained as a yellowish oil.

Workup

  1. temperatureThe mixture was cooled to 0° C
  2. additionAfter the addition
  3. stirringwas stirred at 0° C. for 2 hours 30 minutes
  4. customOrganic and aqueous phases were separated
  5. extractionextracted with 5×80 ml of methylene chloride
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in a rotary evaporator
  9. additionafter addition of 20 mg of BHT
  10. customdried in a fine vacuum
  11. customThe raw product was purified by means of two-fold column chromatography (silica gel 60, 0.035-0.070 mm, ethyl acetate)
  12. custom11.92 g (42.2 mmol; 42%) of the pure product was obtained as a yellowish oil

Sources & evidence

ORD record
ord-bd437c85a7f042ce87985b2f7302152b
Source dataset
uspto-grants-2009_11
Patent number
US07622538B2

Reaction notes

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