Hydrazine hydrate (1:1) → 3-Amino-2-mercapto-3H-quinazolin-4-one

HRID 1924415Notes

Reaction equation

HRID 1924415 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6](OC)=[O:7])=[C:2]=[S:3].O.[NH2:15][NH2:16]>C1COCC1>[NH2:15][N:16]1[C:6](=[O:7])[C:5]2[C:4](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:1][C:2]1=[S:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 85243Benzoic acid, 2-isothiocyanato-, methyl ester

Product 1

HCID 7263833-Amino-2-mercapto-3H-quinazolin-4-oneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-isothiocyanatobenzoate (5.00 g, 25.9 mmol) was dissolved in THF (125 mL), followed by addition of hydrazine monohydrate (2.51 mL, 51.8 mmol). The reaction mixture was refluxed for 1 h, cooled to RT and the precipitate was collected by filtration. The precipitate was washed with water and dried in vacuo to give pure title compound (4.78 g, 96%).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. filtrationthe precipitate was collected by filtration
  3. washThe precipitate was washed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-be37bae17a0448bfa4b1b83fca698439
Source dataset
uspto-grants-2012_05
Patent number
US08178544B2

Reaction notes

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