HCID 19759865, compound → HCID 19759878, compound

HRID 1586871Notes

Reaction equation

HRID 1586871 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1([CH2:16][CH:17]=C)[S:13](=[O:15])(=[O:14])[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[CH2:7]1)=[O:5])[CH3:2].C[OH:20].C(Cl)(Cl)Cl>>[CH2:1]([NH:3][C:4]([C:6]1([CH2:16][CH:17]=[O:20])[S:13](=[O:15])(=[O:14])[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 19759865HCID 19759865, compoundHCID 21584188Chloroform methanol

Product 1

HCID 19759878HCID 19759878, compound

Procedure

N-Ethyl-2-allyl-2,3-dihydrothieno[2,3-b]thiophene-2-carboxamide-1,1-dioxide (7.2 g, 0.025 mol) in 1:1 methanol-chloroform (300 mL) was cooled to -78° C. Ozone was bubbled into the reaction mixture until a pale blue color persisted. The reaction was sparged with nitrogen for 10 minutes and dimethyl sulfide (7 mL) was added. The solution was warmed to room temperature and the solvents removed in vacuo. The residue was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solution was filtered, and the solvent evaporated to give the title compound as an oil (5.3 g).

Workup

  1. customOzone was bubbled into the reaction mixture until a pale blue color
  2. customThe reaction was sparged with nitrogen for 10 minutes
  3. additiondimethyl sulfide (7 mL) was added
  4. customthe solvents removed in vacuo
  5. customThe residue was partitioned between water and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe solution was filtered
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-d081ed34d995407fbd3c490b4a8bc452
Source dataset
uspto-grants-1993_06
Patent number
US05216020

Reaction notes

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