Potassium Carbonate → 2-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamide

HRID 660058Notes

Reaction equation

HRID 660058 reaction equation
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[N:22]=[CH:21][CH:20]=[CH:19][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=[O:11].Br[CH2:24][CH2:25][S:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(OCC)(=O)C.CCCCCC>CN(C=O)C.C(OCC)(=O)C.O>[CH:27]1([S:26][CH2:25][CH2:24][S:7][C:8]2[N:22]=[CH:21][CH:20]=[CH:19][C:9]=2[C:10]([NH:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 22455667((2-Bromoethyl)thio)cyclohexaneHCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

Product 1

HCID 252216282-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamideYield 34%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

607 mg (4.4 mmol) of K2CO3 were added to a solution of 500 mg (2.0 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide (V1) in DMF (5 ml), and the mixture was stirred for 1 h at RT. 446 mg of (2-bromoethyl)-(cyclohexyl)sulfane (crude product V2) were then added, and stirring was continued for a further 18 h at RT. The mixture was then diluted with ethyl acetate, and water was added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. CC (ethyl acetate/n-hexane 1:1) with the residue yielded 268 mg (0.68 mmol, 34%) of 2-(2-(cyclohexylthio)ethylthio)-N-(thiophen-2-ylmethyl)nicotinamide. MS: m/z 393.1 [M+H]+.

Workup

  1. stirringstirring
  2. waitwas continued for a further 18 h at RT
  3. additionwas added
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94ddc86d71c64fd888d40ac1c2768cdd
Source dataset
uspto-grants-2011_12
Patent number
US08084470B2

Reaction notes

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