Ethyl Acetate → 5-Amino-1-(2-fluoroethyl)-1,3-dihydro-2h-2,1-benzisothiazole-2,2-dione

HRID 840197Notes

Reaction equation

HRID 840197 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[CH2:6][S:5]1(=[O:17])=[O:16].CCOC(C)=O>[Pd]>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]2[N:4]([CH2:3][CH2:2][F:1])[S:5](=[O:17])(=[O:16])[CH2:6][C:7]=2[CH:12]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 226227621-(2-Fluoroethyl)-5-nitro-1,3-dihydro-2h-2,1-benzisothiazole-2,2-dione

Product 1

HCID 226227615-Amino-1-(2-fluoroethyl)-1,3-dihydro-2h-2,1-benzisothiazole-2,2-dioneYield 99.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

The product of Step 1 (1.25 g, 4.8 mmol) is dissolved into EtOAc (30 mL) in a Parr bottle and 10% Pd/C (100 mg) added under nitrogen. The mixture is hydrogenated on a Parr apparatus for 4 hrs at 40 psi. Filtration and evaporation of solvent gave a solid (1.1 g, 99%). Mp 119-21° C. HRMS (FAB) calcd for C9H11FN2O2S +H1 231.0603, found 231.0610.

Workup

  1. additionadded under nitrogen
  2. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-32169b0b99264d23a5f0d0c25e42599c
Source dataset
uspto-grants-2002_04
Patent number
US06365612B2

Reaction notes

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