Ethylene Glycol → HCID 86741654, compound

HRID 653462Notes

Reaction equation

HRID 653462 reaction equation
[OH:1][C:2]1[CH2:7][CH2:6][S:5][CH:4]2[S:8][C:9]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:10][C:3]=12.O.[CH2:16](O)[CH2:17][OH:18]>Cl>[OH:18][CH2:17][CH2:16][O:1][C:2]1[CH2:7][CH2:6][S:5][CH:4]2[S:8][C:9]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 86741655HCID 86741655, compound

Product 1

HCID 86741654HCID 86741654, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

5,6-Dihydro-4-hydroxythieno[2,3-b]thiopyran-2-sulfonamide, (2.0 g, 0.008 mole) was dissolved in ethylene glycol (20 ml), treated with concentrated hydrochloric acid (10 drops), and stirred at room temperature for 24 hours. The mixture was poured into water (100 ml) and extracted repeatedly with ethyl acetate. Evaporation of the washed and dried ethyl acetate extract left the crude product as an oily solid. Trituration with 10% ethanol in ether followed by recrystallization of the obtained solid (1.35 g) from ethyl acetate gave 885 mg (37%) of product, m.p. 110°-113° C.

Workup

  1. extractionextracted repeatedly with ethyl acetate
  2. customEvaporation of the
  3. washwashed
  4. extractiondried ethyl acetate extract
  5. waitleft the crude product as an oily solid
  6. customTrituration with 10% ethanol in ether followed by recrystallization of the obtained solid (1.35 g) from ethyl acetate

Sources & evidence

ORD record
ord-01a0371a81ee43caacf0058bd4144e4f
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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