Hydrochloric Acid → 6-Aminobenzothiazole

HRID 617260Notes

Reaction equation

HRID 617260 reaction equation
Cl[Sn]Cl.Cl.[N+:5]([C:8]1[CH:16]=[CH:15][C:11]2[N:12]=[CH:13][S:14][C:10]=2[CH:9]=1)([O-])=O.[OH-].[Na+]>>[NH2:5][C:8]1[CH:16]=[CH:15][C:11]2[N:12]=[CH:13][S:14][C:10]=2[CH:9]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 762566-Nitrobenzothiazole

Product 1

HCID 682886-AminobenzothiazoleYield 96%

Conditions

Temperature
25 °C

Procedure

To a solution of SnCl2 (1.5 g, 1.9 mmol) and 5 mL of con.HCl was added 6-nitrobenzothiazole (0.60 g, 3.4 mmol) in a portion and resulting reaction mixture was stirred for 1 h at 25° C. The reaction mixture was basified with aqueous NaOH and extracted with EtOAc. Combined organic layers were dried over Na2SO4 and concentrated in vacuo, yielding an oil (0.47 g, 3.2 mmol, 96%) which was identified as the amine (>95%) and subjected to the following reaction without further purification.

Workup

  1. customresulting
  2. customreaction mixture
  3. extractionextracted with EtOAc
  4. dry with materialCombined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89659f92c4414c0a9acc8f7bb9498c47
Source dataset
uspto-grants-1999_09
Patent number
US05948804

Reaction notes

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