Hydrochloric Acid → HCID 178527979, compound

HRID 1600442Notes

Reaction equation

HRID 1600442 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[C:6](Cl)(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>N1C=CC=CC=1.O>[SH:4][C:3]1[N:5]=[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:1][N:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 82604Nicotinoyl chlorideHCID 2723789Thiosemicarbazide

Product 1

HCID 178527979HCID 178527979, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 19 g (0.200 mol) of thiosemicarbazide in 175 ml of dry pyridine, 29 g (0.200 mol) of nicotinoyl chloride was slowly added at 10° C. After reflux for 40 min. the reaction mixture was concentrated to half the original volume, 500 ml of water was added, and stored in the cold overnight The precipitate formed was removed by filtration, and the filtrate was evaporated in vacuo. The resulting heavy, yellow oil was dissolved in 300 ml of water, and 64 g (0.600 mol) of sodium carbonate in 400 ml of water was added. After reflux for 4 h the solution was cooled and acidified with conc. hydrochloric acid to pH=4. The formed, colorless precipitate, 65, was isolated by filtration and dried in vacuo. Yield: 35 g (0.297 mol, 98%).

Workup

  1. temperatureAfter reflux for 40 min. the reaction mixture
  2. concentrationwas concentrated to half the original volume, 500 ml of water
  3. additionwas added
  4. customstored in the cold overnight
  5. customformed
  6. customwas removed by filtration
  7. customthe filtrate was evaporated in vacuo
  8. dissolutionThe resulting heavy, yellow oil was dissolved in 300 ml of water
  9. temperatureAfter reflux for 4 h the solution
  10. temperaturewas cooled
  11. customThe formed, colorless precipitate, 65, was isolated by filtration
  12. customdried in vacuo

Sources & evidence

ORD record
ord-a79ba6b2b92347e6908281d09230a7f8
Source dataset
uspto-grants-1999_11
Patent number
USRE036374

Reaction notes

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