Hydrochloric Acid → HCID 14392098, compound

HRID 2291619Notes

Reaction equation

HRID 2291619 reaction equation
[CH2:1]([NH:3][CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])S[C:6]2[S:12][C:13]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:14][C:5]1=2)[CH3:2].Cl.OO[S:22]([O-:24])=[O:23].[K+]>CO.O>[CH2:1]([NH:3][CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[S:22](=[O:24])(=[O:23])[C:6]2[S:12][C:13]([S:15]([NH2:18])(=[O:16])=[O:17])=[CH:14][C:5]1=2)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14392096HCID 14392096, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 14392098HCID 14392098, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 5,6-dihydro-4-ethylamino-6,6-dimethyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide (3.95 g, 0.013 mol) in methanol (85 ml) was acidified with 6.25N methanolic hydrogen chloride (2.1 ml). With stirring, a solution of `OXONE` (11.68 g, 0.019 mol) in water (65 ml) was added over 15 minutes. After stirring at ambient temperature for 17.5 hours, the mixture was filtered and the solid was washed with methanol. The combined filtrate and washings were concentrated in vacuo below 55° C. to remove methanol and the cloudy aqueous solution was basified with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate (150 ml and 2×100 ml), and the combined extracts were washed twice with water, dried over sodium sulfate and evaporated in vacuo. The amorphous residue was converted to the crystalline hydrochloride salt using ethanolic hydrogen chloride to yield 2.16 g (44%) of analytically pure product melting at 255°-255.5° C.

Workup

  1. stirringAfter stirring at ambient temperature for 17.5 hours
  2. filtrationthe mixture was filtered
  3. washthe solid was washed with methanol
  4. concentrationThe combined filtrate and washings were concentrated in vacuo below 55° C.
  5. customto remove methanol
  6. extractionThe mixture was extracted with ethyl acetate (150 ml and 2×100 ml)
  7. washthe combined extracts were washed twice with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-304a54669db64ea98f4084ac2749ca51
Source dataset
uspto-grants-1989_01
Patent number
US04797413

Reaction notes

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