Boron trifluoride etherate → HCID 13472255, compound

HRID 1789131Notes

Reaction equation

HRID 1789131 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[C:17]2[CH2:16][S:15][C:14](=O)[C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].B(F)(F)F.CCOCC>O1CCCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[C:17]2[CH2:16][S:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 13472268HCID 13472268, compound

Product 1

HCID 13472255HCID 13472255, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 8.0 g of 1,3-dihydro-N-(1,1-dimethylethyl)-1-oxobenzo[c]thiophene-4-sulfonamide in a mixture of 15 ml of tetrahydrofuran, 25 ml of boron trifluoride etherate was cooled to 10° under N2, and 56 ml of a 1M solution of borane tetrahydrofuran complex was added dropwise at approximately 10°. The reaction mixture was allowed to warm to ambient temperature as a gas was evolved. When ambient temperature was reached, a slow exotherm to 31° occurred. When the exotherm subsided, the reaction mixture was heated to reflux for two hours, then cooled and allowed to stand overnight. The supernatant was decanted fom some brown solid, and concentrated in vacuo. The resulting yellow oil was cooled to approximately 5°, acidified with 5% hydrochloric acid (gas evolution), and diluted with 150 ml water. The aqueous mixture was extracted with ethyl acetate. The organic solution was washed twice with water, dried over magnesium sulfate, then filtered and the filtrate concentrated in vacuo. The resulting yellow oil was purified by chromatography, using methylene chloride as eluent, to give 3.6 g of 1,3-dihydro-N-(1,1-dimethylethyl)benzo[c]thiophene-4-sulfonamide, m.p. 128.5°-132°.

Workup

  1. temperaturewas cooled to 10° under N2
  2. customWhen ambient temperature
  3. customto 31°
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux for two hours
  6. temperaturecooled
  7. customThe supernatant was decanted fom some brown solid
  8. concentrationconcentrated in vacuo
  9. temperatureThe resulting yellow oil was cooled to approximately 5°
  10. additiondiluted with 150 ml water
  11. extractionThe aqueous mixture was extracted with ethyl acetate
  12. washThe organic solution was washed twice with water
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationthe filtrate concentrated in vacuo
  16. customThe resulting yellow oil was purified by chromatography

Sources & evidence

ORD record
ord-5f3a1c1934ff44819208f12cf8073b61
Source dataset
uspto-grants-1987_08
Patent number
US04687508

Reaction notes

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