HCID 61062518, compound → HCID 178485480, compound

HRID 404764Notes

Reaction equation

HRID 404764 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH3:9])=[O:7])=[CH:4][N:3]=1.[SH2:19].[Na]>CN(C=O)C.C(OCC)(=O)C>[F:16][C:13]1[CH:14]=[CH:15][C:10]([N:8]([CH3:9])[C:6](=[O:7])[C:5]2[CH:17]=[CH:18][C:2]([SH:19])=[N:3][CH:4]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 61062518HCID 61062518, compoundHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 178485480HCID 178485480, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-N-(4-fluoro-phenyl)-N-methyl-nicotinamide (396 mg, 1.5 mmol) was dissolved in anhydrous DMF (6 mL) under nitrogen. Sodium hydrogen sulfide (181 mg, 1.5 mmol) was added and the solution was refluxed for 70 minutes. After cooling, the solution was diluted with ethyl acetate and washed with water. The water was washed with ethyl acetate, and the combined aqueous layers were acidified with 1 N HCl and extracted with ethyl acetate. The combined ethyl acetate layers were washed with water, saturated sodium bicarbonate, water, and brine, dried over sodium sulfate, filtered, and dried in vacu to yield N-(4-Fluoro-phenyl)-6-mercapto-N-methyl-nicotinamide as a yellow solid (283 mg, 72%).

Workup

  1. temperaturethe solution was refluxed for 70 minutes
  2. temperatureAfter cooling
  3. washwashed with water
  4. washThe water was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe combined ethyl acetate layers were washed with water, saturated sodium bicarbonate, water, and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customdried in vacu

Sources & evidence

ORD record
ord-f960fbe77d3f47d7bbdcf4e978c2972b
Source dataset
uspto-grants-2014_06
Patent number
US08748623B2

Reaction notes

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