Hydrochloric Acid → 7-Methyl-1,3-benzothiazol-6-amine

HRID 617263Notes

Reaction equation

HRID 617263 reaction equation
Cl[Sn]Cl.Cl.[CH3:5][C:6]1[C:14]2[S:13][CH:12]=[N:11][C:10]=2[CH:9]=[CH:8][C:7]=1[N+:15]([O-])=O.[OH-].[Na+]>>[CH3:5][C:6]1[C:14]2[S:13][CH:12]=[N:11][C:10]=2[CH:9]=[CH:8][C:7]=1[NH2:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 125888347-Methyl-6-nitro-1,3-benzothiazole

Product 1

HCID 218751347-Methyl-1,3-benzothiazol-6-amineYield 113.1%

Conditions

Temperature
25 °C

Procedure

To a solution of SnCl2 (3.0 g, 3.8 mmol) and 10 mL of con.HCl was added 7-methyl-6-nitrobenzothiazole (0.68 g, 3.5 mmol) in a portion and the resulting reaction mixture was stirred for 1 h at 25° C. The reaction mixture was basified with aqueous NaOH and extracted with EtOAc and CHCl3. Combined organic layers were dried over Na2SO4 and concentrated in vacuo, yielding an oil (0.65 g, >95%) which was identified as the desired amine and subjected to a following reaction without further purification.

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc and CHCl3
  3. dry with materialCombined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43493e5c7c8b48b58e0f3b047d81d22b
Source dataset
uspto-grants-1999_09
Patent number
US05948804

Reaction notes

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