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

HRID 2300399Notes

Reaction equation

HRID 2300399 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-cee1e85c2ed94f8e9ec42c06351d53db
Source dataset
uspto-grants-2002_12
Patent number
US06498177B2

Reaction notes

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