Potassium Carbonate → HCID 59487294, compound

HRID 1925556Notes

Reaction equation

HRID 1925556 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:18][C:19]([CH3:33])([CH3:32])[CH2:20][CH2:21][NH:22][C:23](=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][C:25]=1[SH:30].CCCCCC.CC(=O)OCC>CC(C)=O>[CH3:18][C:19]([CH3:33])([CH3:32])[CH2:20][CH2:21][NH:22][C:23]([C:24]1[C:25]([S:30][CH2:8][C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:31]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2363491-Chloro-3-phenylpropan-2-oneHCID 21226206Ethyl acetate hexaneHCID 178444849HCID 178444849, compound

Product 1

HCID 59487294HCID 59487294, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

840 mg (6.1 mmol) of K2CO3 and 340 mg (2.0 mmol) of 1-chloro-3-phenylpropan-2-one were added to a solution of 450 mg (2.0 mmol) of N-(3,3-dimethylbutyl)-2-mercapto-nicotinamide in acetone (10 ml), and the mixture was then heated for 1 h at 50° C. Dilution with water (20 ml) and extraction with EA (2×30 ml) were then carried out. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 4:1) of the residue yielded 420 mg (1.1 mmol, 56%) of N-(3,3-dimethyl-butyl)-2-[(2-oxo-3-phenyl-propyl)sulfanyl]-pyridine-3-carboxylic acid amide. MS: m/z 371.2 [M+H]+.

Workup

  1. extractionDilution with water (20 ml) and extraction with EA (2×30 ml)
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a5fdf6534194d2ba3488110761fbb50
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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