Water → 1-[4-(4-Mercaptobutylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one

HRID 376971

Reaction equation

HRID 376971 reaction equation
Cl[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]([SH:24])[CH2:20][CH2:21][CH2:22][SH:23].C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[SH:23][CH2:22][CH2:21][CH2:20][CH2:19][S:24][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

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 791481,4-ButanedithiolHCID 157024081-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

Product 1

HCID 193606151-[4-(4-Mercaptobutylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

40 g (0.15 mol) of 1-(4-chlorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one and 109 g (0.89 mol) of 1,4-butanedithiol are dissolved in 300 ml of dimethylacetamide, and the solution is stirred at around 100° C. together with 41 g of potassium carbonate for 5 h. Then the solution is cooled to room temperature and poured into water. The crude product is extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate -hexane (20:80) as an eluent. Melting point 98 ° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.31 (s, 6H), 1.36 (t, 1H), 1.76-1.90 (m, 4H), 2.53-2.62 (m, 6H), 2.98-3.04 (m, 2H), 3.69 (t, 4H), 7.25 (d, 2H), 8.50 (d, 2H).

Workup

  1. extractionThe crude product is extracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography on silica gel with ethyl acetate -hexane (20:80) as an eluent

Sources & evidence

ORD record
ord-179104a951b34286bb7623e5ec05b593
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Linked notes

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