Hydrochloric Acid → 2-Methyl-2-(morpholin-4-yl)-1-(4-sulfanylphenyl)propan-1-one

HRID 1380602Notes

Reaction equation

HRID 1380602 reaction equation
C1(C)C=CC=CC=1.Cl[C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:25])[C:16]([CH3:24])([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH3:17])=[CH:11][CH:10]=1.Cl.[SH2:27]>CN1CCCC1=O.O>[SH:27][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:25])[C:16]([CH3:24])([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH3:17])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 402Hydrogen SulfideHCID 1140TolueneHCID 157024081-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

Product 1

HCID 157024042-Methyl-2-(morpholin-4-yl)-1-(4-sulfanylphenyl)propan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

451 g of hydrated sodium sulfide (Na2S content 32-38%≈2 mols) are suspended in 800 ml of N-methyl-2-pyrrolidone and 400 ml of toluene and the mixture is warmed to 130°. Approx. 290 ml of water are removed in a water separator, and the toluene is then removed by distillation. 100 g (0.37 mol) of 1-(4-chlorophenyl)-2-methyl-2-morpholinopropan-1-one are introduced into the warm solution in portions, and the suspension is heated at 140° for 12 hours. After cooling, the pH of the reaction mixture is adjusted to 6 by adding 6N HCl, and the solution is freed from H2S. The solution is then diluted with 1 liter of water and extracted with diethyl ether. The ether extracts are extracted by shaking several times with 20% sodium hydroxide solution, and the combined aqueous alkaline extracts are neutralised with 6N HCl and extracted by shaking with diethyl ether. The ether extracts are dried over MgSO4 and concentrated. The oil which remains is crystallised from cyclohexane. Melting point 68°-69° C. (Compound No. 22).

Workup

  1. customApprox. 290 ml of water are removed in a water separator
  2. customthe toluene is then removed by distillation
  3. temperaturethe suspension is heated at 140° for 12 hours
  4. temperatureAfter cooling
  5. extractionextracted with diethyl ether
  6. extractionThe ether extracts are extracted
  7. extractionextracted
  8. stirringby shaking with diethyl ether
  9. dry with materialThe ether extracts are dried over MgSO4
  10. concentrationconcentrated
  11. customThe oil which remains is crystallised from cyclohexane

Sources & evidence

ORD record
ord-a9fa3d33c8354f95a68aac1449301c0d
Source dataset
uspto-grants-1986_04
Patent number
US04582862

Reaction notes

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