Hydrazine hydrate (1:1) → 4-Amino-3-sulfanylbenzonitrile

HRID 70427Notes

Reaction equation

HRID 70427 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]2[N:7]=C[S:9][C:5]=2[CH:4]=1)#[N:2].O.NN>CCO>[NH2:7][C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[SH:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10607144Benzothiazole-6-carbonitrile

Product 1

HCID 155439364-Amino-3-sulfanylbenzonitrileYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-cyanobenzothiazole (532 mg, 3.33 mmol) and hydrazine monohydrate (1.2 ml, 24.76 mmol) in EtOH (10 ml) was heated at 80° C. under N2 atmosphere for 2 hours. The solvent was evaporated, H2O was added to the residue, and the solution was adjusted to pH˜5-7 with AcOH. The resulting yellow precipitate was filtered and washed with H2O, dried under high vacuum to yield the title compound as yellow solid (486 mg, 97%).

Workup

  1. customThe solvent was evaporated
  2. additionH2O was added to the residue
  3. filtrationThe resulting yellow precipitate was filtered
  4. washwashed with H2O
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-472d36f42e8f4b9a91bbdac353302057
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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