Allyl bromide → 2-Methyl-2-(morpholin-4-yl)-1-{4-[(prop-2-en-1-yl)sulfanyl]phenyl}propan-1-one

HRID 1380603Notes

Reaction equation

HRID 1380603 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([CH3:17])([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1.[CH2:19](Br)[CH:20]=[CH2:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:21]([S:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([CH3:10])([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH3:17])=[CH:4][CH:3]=1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 157024042-Methyl-2-(morpholin-4-yl)-1-(4-sulfanylphenyl)propan-1-one

Product 1

HCID 233256812-Methyl-2-(morpholin-4-yl)-1-{4-[(prop-2-en-1-yl)sulfanyl]phenyl}propan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g (0.38 mol) of 1-(4-mercaptophenyl)-2-methyl-2-morpholinopropan-1-one, 5 g (0.041 mol) of freshly distilled allylbromide and 5.2 g (0.038 mol) of dry potassium carbonate are suspended in 50 ml of acetone and the mixture is heated to reflux temperature for 16 hours. After cooling, the solvent is removed by distillation, water and diethyl ether are added to the residue, and the water phase is extracted with ether. The organic phase is washed with 10% NaOH solution and water, dried over MgSO4 and concentrated. The oil which remains is distilled in a bulb tube at 180°-200° C./13 Pa. (Compound No. 23).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux temperature for 16 hours
  3. temperatureAfter cooling
  4. customthe solvent is removed by distillation, water and diethyl ether
  5. additionare added to the residue
  6. extractionthe water phase is extracted with ether
  7. washThe organic phase is washed with 10% NaOH solution and water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. distillationThe oil which remains is distilled in a bulb tube at 180°-200° C./13 Pa

Sources & evidence

ORD record
ord-b82f6e8826624f98bc1f243d34221af4
Source dataset
uspto-grants-1986_04
Patent number
US04582862

Reaction notes

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