Hydrochloric Acid → HCID 13911591, compound

HRID 653453Notes

Reaction equation

HRID 653453 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][S:6][C:5]2[S:8][C:9]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:10][C:4]=2[C:3]1=[O:15].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[OH:15][CH:3]1[C:2]([CH3:16])([CH3:1])[CH2:7][S:6][C:5]2[S:8][C:9]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:10][C:4]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 13911587HCID 13911587, compound

Product 1

HCID 13911591HCID 13911591, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5,6-dihydro-5,5-dimethyl-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide (12.8 g, 0.046 m) and sodium borohydride (2.27 g, 0.060 m) in ethanol (460 ml) was stirred under reflux for 1 hour. After cooling to ambient temperature, the mixture was acidified by the rapid addition of 1N hydrochloric acid (65 ml), then rendered basic with saturated sodium bicarbonate solution and concentrated in vacuo to remove ethanol. The aqueous suspension was distributed between ethyl acetate (300 ml) and water (200 ml), the aqueous layer was separated and extracted with ethyl acetate (2×300 ml), the combined ethyl acetate layers were washed with saturated sodium bicarbonate solution, twice with water and dried over sodium sulfate. The solvent was evaporated under reduced pressure to yield 11.71 g (91%) of product. An analytical sample melted at 158°-159° C. after recrystallization from nitromethane.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationconcentrated in vacuo
  3. customto remove ethanol
  4. customthe aqueous layer was separated
  5. extractionextracted with ethyl acetate (2×300 ml)
  6. washthe combined ethyl acetate layers were washed with saturated sodium bicarbonate solution, twice with water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e7074e613bb540e09fa497589ead53f2
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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