2-Amino-6-nitrobenzothiazole → 2,6-Benzothiazolediamine

HRID 1761457Notes

Reaction equation

HRID 1761457 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:5]=2[N:6]=1>O1CCCC1.[Ni]>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 1

HCID 227042-Amino-6-nitrobenzothiazole

Product 1

HCID 215042,6-BenzothiazolediamineYield 50%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-6-nitrobenzothiazole (10 g, 0.051 mol) in 100 mL of tetrahydrofuran was added 3.0 g Raney-nickel active catalyst. The reaction mixture was hydrogenated until hydrogen consumption ceased. The reaction mixture was filtered through a Celite pad and the solution was concentrated under reduced pressure to produce a brown solid. The solid was recrystallized from toluene, yielding 2,6-diaminobenzothiazole (50% yield, m.p. 202°-203° C.).

Workup

  1. customThe reaction mixture was hydrogenated until hydrogen consumption
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. concentrationthe solution was concentrated under reduced pressure
  4. customto produce a brown solid
  5. customThe solid was recrystallized from toluene

Sources & evidence

ORD record
ord-10da42dd56d34dfaa052558e821fb0e2
Source dataset
uspto-grants-1989_05
Patent number
US04826860

Reaction notes

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