Stannous chloride dihydrate → 4-(6-Methoxy-1,3-benzothiazol-2-yl)aniline

HRID 916515Notes

Reaction equation

HRID 916515 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1.O.O.[Sn](Cl)Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=3)[S:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 106608526-Methoxy-2-(4-nitrophenyl) benzothiazole

Product 1

HCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the 6-methoxy-2-(4-nitropheyl)benzothiazoles 5 (22 mg, 0.077 mmol) and tin(II) chloride dihydrate (132 mg, 0.45 mmol) in boiling ethanol was stirred under nitrogen for 4 hrs. Ethanol was evaporated and the residue was dissolved in ethyl acetate (10 mL), washed with 1 N sodium hydroxide (2 mL) and water (5 mL), and dried over MgSO4. Evaporation of the solvent gave 19 mg (97%) of the product 6 as yellow solid.

Workup

  1. customEthanol was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (10 mL)
  3. washwashed with 1 N sodium hydroxide (2 mL) and water (5 mL)
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0250a7e9c830452bbb2e5330fc28f97d
Source dataset
uspto-grants-2007_09
Patent number
US07270800B2

Reaction notes

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