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

HRID 2279250Notes

Reaction equation

HRID 2279250 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>CCO>[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 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-Nitrobenzo[d]thiazole (5a) (10 g, 55.5 mmol) in EtOH (100 mL), Hydrazine hydrate (39 g, 77.9 mmol) was added at room temperature under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 h. After completion of the reaction (by TLC) the volatiles were removed under reduced pressure, the residue was neutralized with 1N HCl (100 mL) and extracted with EtOAc (3×150 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to afford 2-Amino-5-nitrobenzenethiol (5b) (7.0 g, crude). The crude material was taken to the next step without purification.

Workup

  1. customAfter completion of the reaction (by TLC) the volatiles
  2. customwere removed under reduced pressure
  3. extractionextracted with EtOAc (3×150 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b171e2241ee744aaa67dfc4bf1b1b426
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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