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Potassium Carbonate → 1-[4-(10-Mercaptodecanylthio)-phenyl]-2-methyl-2-morpholine-4-yl-propane-1-one

HRID 376970
Notes
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Reaction equation

HRID 376970 reaction equation
[CH2:1]([SH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][SH:11].C(=O)([O-])[O-].[K+].[K+].Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:36])[C:27]([CH3:35])([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH3:28])=[CH:22][CH:21]=1>CC(N(C)C)=O>[SH:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11][C:20]1[CH:21]=[CH:22][C:23]([C:26](=[O:36])[C:27]([CH3:28])([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[CH3:35])=[CH:24][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 144941,10-DecanedithiolHCID 157024081-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

Product 1

HCID 193606111-[4-(10-Mercaptodecanylthio)-phenyl]-2-methyl-2-morpholine-4-yl-propane-1-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
85 °C

Procedure

51.7 g (0.25 mol) of 1,10-decanedithiol are added to a suspension of 13.9 g (0.10 mol) of potassium carbonate in 50 ml of dimethylacetamide. The suspension is heated to 85° C., and a solution of 13.4 g (0.05 mol) of 1-(4-chlorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one in 25 ml of dimethylacetamide is added dropwise over 5 h. After stirring for 18 h, the solid is filtered off, the filtrate is poured into 30 ml of 2N HCl solution. The formed white precipitate is collected by filtration and then dissolved in methylene chloride and neutralized with 30 ml of 2N NaOH solution. After methylene chloride is distilled off, the residual crystals are further purified by recrystallization from chloroform-ethanol (20:80). The obtained product has a melting point of 87-90° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.28-1.39 (m, 9H), 1.45 (m, 2H),1.31 (s, 6H), 1.64 (q, 4H), 1.69 (m, 2H), 2.52 (q, 2H), 2.56 (m, 4H), 2.99 (m, 2H), 3.71 (m, 4H), 7.26 (d, 2H), 8.49 (d, 2H).

Workup

  1. filtrationthe solid is filtered off
  2. additionthe filtrate is poured into 30 ml of 2N HCl solution
  3. filtrationThe formed white precipitate is collected by filtration
  4. dissolutiondissolved in methylene chloride and neutralized with 30 ml of 2N NaOH solution
  5. distillationAfter methylene chloride is distilled off
  6. customthe residual crystals are further purified by recrystallization from chloroform-ethanol (20:80)

Sources & evidence

ORD record
ord-3f3f2f9dd2bc40768f3401aa957ea68b
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06022906

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes