Isatoic Anhydride → Semicarbazide, 1-(o-aminobenzoyl)-3-thio-

HRID 2229162Notes

Reaction equation

HRID 2229162 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)O[C:2]2=[O:3].[NH2:13][NH:14][C:15]([NH2:17])=[S:16]>CN(C=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:13][NH:14][C:15]([NH2:17])=[S:16])=[O:3]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 2723789Thiosemicarbazide

Product 1

HCID 3057327Semicarbazide, 1-(o-aminobenzoyl)-3-thio-Yield 46.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Isatoic anhydride (4.9 g) and thiosemicarbazide (2.8 g) were dissolved in 30 ml of DMF and the resulting mixture was stirred 20 h at 60 to 80° C. The solvent was removed under reduced pressure and the residue was recrystallized from methanol and ethanol to give 2.94 g of 1-(2-aminobenzoyl)thiosemicarbazide.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was recrystallized from methanol and ethanol

Sources & evidence

ORD record
ord-fac37f686fbd41939c3484eb3d22f219
Source dataset
uspto-grants-2002_07
Patent number
US06420367B1

Reaction notes

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