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

HRID 421291Notes

Reaction equation

HRID 421291 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.[H][H]>CO.[Pd]>[S:3]1[C:4]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH2:1]

Participants

5

Reactant 2

HCID 227042-Amino-6-nitrobenzothiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 215042,6-BenzothiazolediamineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Amino-6-nitrobenzothiazole (1.0 g, 5.12 mmol) was dissolved in 100 ml of MeOH and palladium on activated carbon (10%, 545 mg, 0.51 mmol) was added. The reaction mixture was hydrogenated using hydrogen at RT (3 bar H2) for 2.5 h. The mixture was filtered, the solvent was removed under reduced pressure and the residue was purified using silica gel chromatography (ethyl acetate:n-heptane 1:2). 0.81 g (yield: 96%) of the purified title compound was obtained.

Workup

  1. customat RT
  2. customfor 2.5 h
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified
  6. custom0.81 g (yield: 96%) of the purified title compound
  7. customwas obtained

Sources & evidence

ORD record
ord-33d67ecb6f9447b3a700208fec01f7c7
Source dataset
uspto-grants-2012_01
Patent number
US08097758B2

Reaction notes

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