Stannous chloride dihydrate → 2-(4-Aminophenyl)benzothiazole

HRID 1950670Notes

Reaction equation

HRID 1950670 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 8275002-(4-Nitrophenyl)Benzo[D]Thiazole

Product 1

HCID 2344752-(4-Aminophenyl)benzothiazoleYield 112.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-nitrophenyl)benzothiazole (105 mg, 0.40 mmol) and tin(II) chloride dihydrate (205 mg, 0.91 mmol) in ethanol (20 mL) was refluxed under N2 for 4 hrs. After removing ethanol by vacuum evaporation. The residue was dissolved into ethyl acetate (20 ml), and washed with NaOH solution (1N, 3×20 ml) and water (3×20 ml), dried and evaporated to dryness to give 102 mg (97%) of the product

Workup

  1. temperaturewas refluxed under N2 for 4 hrs
  2. customAfter removing ethanol
  3. customby vacuum evaporation
  4. dissolutionThe residue was dissolved into ethyl acetate (20 ml)
  5. washwashed with NaOH solution (1N, 3×20 ml) and water (3×20 ml)
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-24b20bc3eaec4f25b01182de9139a0d1
Source dataset
uspto-grants-2013_03
Patent number
US08404213B2

Reaction notes

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