Water → HCID 18533028, compound

HRID 413325Notes

Reaction equation

HRID 413325 reaction equation
[SH2:1].[Na].Cl[C:4]1[CH:17]=[CH:16][C:7]([C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1.O>CN(C=O)C>[SH:1][C:4]1[CH:17]=[CH:16][C:7]([C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 985034-(4'-Chlorobenzoyl)pyridineHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 18533028HCID 18533028, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of sodium hydrogen sulfide (6 g) in DMF (100 ml) was heated to reflux for 1 h, then cooled and 4-(4-chlorobenzoyl)pyridine (5 g) was added. The mixture was heated at reflux for 2 h, then cooled and added to water. The brown solution was washed with ether, then acidified with citric acid and extracted with dichloromethane (2×100 ml). The solvent was dried and evaporated to give the title compound as beige powder (2.4 g, 50%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. temperaturecooled
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 2 h
  6. temperaturecooled
  7. washThe brown solution was washed with ether
  8. extractionextracted with dichloromethane (2×100 ml)
  9. customThe solvent was dried
  10. customevaporated

Sources & evidence

ORD record
ord-92bcd9ecb18a4aeb9e09d4d631155c39
Source dataset
uspto-grants-2003_05
Patent number
US06566384B1

Reaction notes

Loading…