Potassium Carbonate → HCID 46908820, compound

HRID 2044160Notes

Reaction equation

HRID 2044160 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].Cl[CH2:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27]>CN(C=O)C>[O:27]=[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:25][CH2:24][S:7][C:8]1[C:9]([C:10]([NH:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[O:11])=[CH:19][CH:20]=[CH:21][N:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 702953-ChloropropiophenoneHCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

Product 1

HCID 46908820HCID 46908820, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

227 mg (1.65 mmol) of K2CO3 were added to a solution of 375 mg (1.5 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide in DMF (3.5 ml), and stirring was carried out for 30 min at RT. 252 mg (1.5 mmol) of 3-chloro-1-phenylpropan-1-one were then added and stirring was carried out for a further 2 d at RT. The mixture was then concentrated in vacuo and the residue was taken up in a mixture of EA and a 1N aq. NaHCO3 sol. The organic phase was separated off and the aqueous phase was extracted again with EA. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by means of CC (EA/hex 1:1), and subsequent crystallization (EA/hexane) yielded 73 mg (0.2 mmol, 13%) of 2-[(3-oxo-3-phenyl-propyl)sulfanyl]-N-(thiophen-2-yl-methyl)-pyridine-3-carboxylic acid amide. MS: m/z 383.1 [M+H]+.

Workup

  1. stirringstirring
  2. waitwas carried out for a further 2 d at RT
  3. concentrationThe mixture was then concentrated in vacuo
  4. additionthe residue was taken up in a mixture of EA
  5. customa 1N aq. NaHCO3 sol. The organic phase was separated off
  6. extractionthe aqueous phase was extracted again with EA
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by means of CC (EA/hex 1:1), and subsequent crystallization (EA/hexane)

Sources & evidence

ORD record
ord-d53fa4b2717e4a7eb5eae89618c6d1b3
Source dataset
uspto-grants-2013_11
Patent number
US08586755B2

Reaction notes

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