Tetrahydrofuran → HCID 13472236, compound

HRID 483055Notes

Reaction equation

HRID 483055 reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].[OH-].[NH4+:7].[O:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH2:9]1[C:10]2[CH:9]=[CH:10][CH:11]=[C:12]([S:1]([NH2:7])(=[O:3])=[O:2])[C:11]=2[CH2:12][O:8]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 24648Sulfuryl chloride

Product 1

HCID 13472236HCID 13472236, compound

Procedure

A solution of 9.8 g of the sulfonyl chloride, prepared in Part A, in 150 ml tetrahydrofuran was cooled to approximately 5°, and 6.6 ml of concentrated ammonium hydroxide was added dropwise. The resulting yellow suspension was allowed to warm to ambient temperature and stirred 0.5 hour; thin-layer chromatography showed the reaction was complete. The solvent was evaporated in vacuo and the resulting solid was slurried in 150 ml water, collected, washed with water and dried. The crude product was washed with 1-chlorobutane and dried to give 7.74 g of 1,3-dihydrobenzo[c]furan-4-sulfonamide, m.p. 153°-158°.

Workup

  1. temperaturewas cooled to approximately 5°
  2. customThe solvent was evaporated in vacuo
  3. customcollected
  4. washwashed with water
  5. customdried
  6. washThe crude product was washed with 1-chlorobutane
  7. customdried

Sources & evidence

ORD record
ord-150e1381f12541dfb9d8be5ded0788fc
Source dataset
uspto-grants-1986_03
Patent number
US04578108

Reaction notes

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