Ethanol → 5-Amino-3-(1-methylpyrrol-2-yl)-1,2-benzisothiazole

HRID 48961Notes

Reaction equation

HRID 48961 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[C:11]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:10]=2[S:9][N:8]=1.C(O)C.O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]2[S:9][N:8]=[C:7]([C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=3)[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 20634261HCID 20634261, compound

Product 1

HCID 206342755-Amino-3-(1-methylpyrrol-2-yl)-1,2-benzisothiazoleYield 84.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 3-(1-methylpyrrol-2-yl)-5-nitro-1,2-benzisothiazole(1.5 g, 5.79 mmol), ethyl acetate and ethanol is added tin(II) chloride dihydrate (6.5 g, 28.8 mmol). The resultant mixture is heated to reflux, stirred 30 min at reflux and cooled to room temperature. The mixture is diluted with ethyl acetate and slowly quenched with solid sodium bicarbonate and water. Brine is added and the resultant mixture stirred and allowed to stand until layer separation is complete. The organic layer is saved and the aqueous layer is extracted with ethyl acetate. The solids which form in the aqueous layer are triturated with ethyl acetate, filtered and the filtrate combined with the above organic layers. The combined organic layers are washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to afford the title compound as a brown oil (1.10 g, 84.6%) identified by NMR spectral analysis.

Workup

  1. temperatureto reflux
  2. temperatureat reflux
  3. customslowly quenched with solid sodium bicarbonate and water
  4. additionBrine is added
  5. stirringthe resultant mixture stirred
  6. customto stand until layer separation
  7. extractionthe aqueous layer is extracted with ethyl acetate
  8. customThe solids which form in the aqueous layer
  9. customare triturated with ethyl acetate
  10. filtrationfiltered
  11. washThe combined organic layers are washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a19775137204567adcb68126f6ee4a3
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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