Water → HCID 70383598, compound

HRID 653459Notes

Reaction equation

HRID 653459 reaction equation
[S:1]1[C:5]2[S:6][CH2:7][CH2:8][C:9](=[O:10])[C:4]=2[CH:3]=[C:2]1[S:11]([NH2:14])(=[O:13])=[O:12].C1C=C[NH+]=CC=1.[Br:21][Br-]Br.O>O1CCCC1.C(#N)C>[Br:21][CH:8]1[CH2:7][S:6][C:5]2[S:1][C:2]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:3][C:4]=2[C:9]1=[O:10]

Participants

5

Reactant 2

HCID 962WaterHCID 137631454-Oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide

Product 1

HCID 70383598HCID 70383598, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide (3.50 g, 0.014 m) in dry tetrahydrofuran (70 ml) was stirred at ambient temperature while a solution of pyridinium bromide perbromide (6.08 g, 0.019 m) in dry tetrahydrofuran (35 ml) and acetonitrile (10 ml) was added over 15 minutes. After stirring at ambient temperature for 1 hour, the reaction mixture was added to water (100 ml) and concentrated in vacuo to remove tetrahydrofuran and acetonitrile. The aqueous mixture was extracted with ethyl acetate (3×100 ml), the combined extracts were washed with water, dried over sodium sulfate and concentrated to dryness in vacuo. The residue was partially purified by chromatography on silica gel, eluting with 50% ethyl acetate-hexane, to yield 3.68 g (80%) of material which was used in the next reaction without further purification.

Workup

  1. additionwas added over 15 minutes
  2. concentrationconcentrated in vacuo
  3. customto remove tetrahydrofuran and acetonitrile
  4. extractionThe aqueous mixture was extracted with ethyl acetate (3×100 ml)
  5. washthe combined extracts were washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness in vacuo
  8. customThe residue was partially purified by chromatography on silica gel
  9. washeluting with 50% ethyl acetate-hexane

Sources & evidence

ORD record
ord-f4705b7eb15440c3ac13f1bc5bffb4d7
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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