Stannous chloride dihydrate → 2-(2,4-Dimethylphenoxy)-1,3-benzothiazol-7-amine

HRID 2235504Notes

Reaction equation

HRID 2235504 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[S:6][C:7]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.O.O.[Sn](Cl)Cl>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[S:6][C:7]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 685813382-(2,4-Dimethylphenoxy)-7-nitro-1,3-benzothiazole

Product 1

HCID 685813992-(2,4-Dimethylphenoxy)-1,3-benzothiazol-7-amineYield 114%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2,4-dimethylphenoxy)-7-nitro-1,3-benzothiazole (220 mg, 0.733 mmol) and tin(II) chloride dihydrate (694 mg, 3.66 mmol) in DMF (10 ml) was stirred at 80° C. for 15 h and diluted with saturated NaHCO3 solution. The aqueous solution was extracted with AcOEt. The extract was washed with brine, dried over Magnesium sulfate, and concentrated under vacuum. The residue was purified by chromatography eluting with 10% AcOEt in n-hexane to afford 226 mg of the title compound.

Workup

  1. extractionThe aqueous solution was extracted with AcOEt
  2. washThe extract was washed with brine
  3. dry with materialdried over Magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography
  6. washeluting with 10% AcOEt in n-hexane

Sources & evidence

ORD record
ord-460d428c2de7416b8b49efe3904bb172
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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