Stannous chloride dihydrate → 1,3-Benzothiazole-2,5-diamine

HRID 723951Notes

Reaction equation

HRID 723951 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([NH2:12])=[N:9][C:8]=2[CH:13]=1)([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([NH2:12])=[N:9][C:8]=2[CH:13]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 27547595-Nitro-1,3-benzothiazol-2-amine

Product 1

HCID 7685251,3-Benzothiazole-2,5-diamineYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethanol (36 mL) was added 5-nitro-benzothiazol-2-ylamine (Example 15, 78 mg, 0.35 mmol) and tin dichloride dihydrate (449 mg, 2 mmol). The resulting mixture was heated at 80° C. for 4 hours. The solution was cooled to room temperature and the solvent was removed. The residue was dissolved in ethyl acetate and poured onto 50 mL of 1.5 N NaOH solution and extracted using ethyl acetate (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to give a solid (43 mg, 66%). 1H NMR (DMSO d) δ: 7.23–7.19 (m, 3H), 6.59 (d, 1H, J=1.96 Hz), 6.32 (dd, 1H, J=2.18, 8.28 Hz), 4.88 (br s, 2H); MS (ESI) 166 (M+1, 100%).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. additionpoured onto 50 mL of 1.5 N NaOH solution
  5. extractionextracted
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3c520c8433f740a380a66b56fe1e10a3
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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