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

HRID 1372435Notes

Reaction equation

HRID 1372435 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]>[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

5

Reactant 2

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

Product 1

HCID 215042,6-BenzothiazolediamineYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

2-Amino-6-nitrobenzothiazole (500 mg, 2.56 mmol) was dissolved in methanol (20 mL) and 10% palladium on carbon (50 mg) was added as a slurry in methanol (1 mL). The atmosphere was replaced with hydrogen and the suspension was stirred overnight. The catalyst was removed by suction filtration and the solvent evaporated to afford 2,6-diaminobenzothiazole (420 mg, 99%) as a pale yellow solid.

Workup

  1. customThe catalyst was removed by suction filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-e6c6e6c47b924d8a9a6d0a379b0a8a6a
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

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