Ammonium Hydroxide → 6-Aminobenzothiazole

HRID 1519751Notes

Reaction equation

HRID 1519751 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[N:8]=[CH:9][S:10][C:6]=2[CH:5]=1)([O-])=O.Cl[Sn]Cl.[NH4+].[OH-]>Cl>[S:10]1[C:6]2[CH:5]=[C:4]([NH2:1])[CH:12]=[CH:11][C:7]=2[N:8]=[CH:9]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24479Stannous ChlorideHCID 762566-Nitrobenzothiazole

Product 1

HCID 682886-AminobenzothiazoleYield 99.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 6-nitrobenzothiazole (3.8 g, 0.02 mol) in 40 ml 2N HCl was added SnCl2 (15.9 g, 0.06 mol), and the mixture was stirred at room temperature overnight. The reaction mixture was treated with concentrated NH4OH to pH 11 and extracted with ethyl acetate (3×150 ml). The combined organic phase was concentrated under reduced pressure. The residue was purified (silica gel chromatography) to give benzo[d]thiazol-6-amine (3 g, 72%).

Workup

  1. extractionextracted with ethyl acetate (3×150 ml)
  2. concentrationThe combined organic phase was concentrated under reduced pressure
  3. customThe residue was purified (silica gel chromatography)

Sources & evidence

ORD record
ord-7a126e2f709a4cf7aa5ee30e262743f4
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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