Hydrazine hydrate (1:1) → 2-Amino-5-nitrobenzenethiol

HRID 1991286Notes

Reaction equation

HRID 1991286 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=C[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].O.NN>C(O)C>[NH2:8][C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[SH:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 762566-Nitrobenzothiazole

Product 1

HCID 109866912-Amino-5-nitrobenzenethiolYield 102.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 6-nitrobenzothiazole (30 g, 0.1665 mol) in ethanol (500 mL) is added 100% hydrazine hydrate (60.2 mL, 1.931 mol). The mixture is refluxed for 2 h at which time the solution turns red. The reaction is quenched by the addition of ice cold conc. HCl until the red color disappears. The resulting solid is filtered, washed with water (25 mL) and dried under high vacuum to give the title compound as a yellow solid (28.96 g, 84%), MS m/z 171.5 (M+H)+.

Workup

  1. temperatureThe mixture is refluxed for 2 h at which time the solution
  2. customThe reaction is quenched by the addition of ice cold conc. HCl until the red color
  3. filtrationThe resulting solid is filtered
  4. washwashed with water (25 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-e391af7e2790468ca22422e9c8621e52
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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