Thiosemicarbazide → HCID 57991941, compound

HRID 2075355Notes

Reaction equation

HRID 2075355 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=O)[C:5]=2[CH:4]=[N:3][N:2]=1.[NH2:14][NH:15][C:16]([NH2:18])=[S:17]>CN(C=O)C>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([NH:14][NH:15][C:16]([NH2:18])=[S:17])=[O:13])[C:5]=2[CH:4]=[N:3][N:2]=1

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 57991901Phthalazine-5-carboxylic acid

Product 1

HCID 57991941HCID 57991941, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a 100 mL round bottom flask was added phthalazine-5-carboxylic acid (0.50 g, 2.9 mmol) 1,1′-carbonyldiimidazole (0.93 g, 5.7 mmol) and DMF (2.2 mL). The mixture was stirred at 70° C. for 1 hour and treated with thiosemicarbazide (0.81 g, 8.9 mmol). The resulting mixture was stirred at 70° C. for 30 minutes. The mixture was concentrated under vacuum to remove almost all of the DMF. The remaining residue was treated with 2 N HCl with stirring until the solution reached pH 4. Upon standing, a yellow solid formed. The precipitate was recovered by filtration, washing with water and air dried to provide 1-(phthalazine-5-carbonyl)thiosemicarbazide (0.45 g, 63%).

Workup

  1. stirringThe resulting mixture was stirred at 70° C. for 30 minutes
  2. concentrationThe mixture was concentrated under vacuum
  3. customto remove almost all of the DMF
  4. additionThe remaining residue was treated with 2 N HCl
  5. stirringwith stirring until the solution
  6. customa yellow solid formed
  7. filtrationThe precipitate was recovered by filtration
  8. washwashing with water and air
  9. customdried

Sources & evidence

ORD record
ord-a1f3af060daf44efad8482c81b17d8c5
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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