Carbon Dioxide → HCID 14254943, compound

HRID 1252355Notes

Reaction equation

HRID 1252355 reaction equation
[CH2:1]([S:4][C:5]1[C:6]([S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[CH:7][S:8][CH:9]=1)[CH2:2][CH3:3].C([Li])CCC.[C:23](=[O:25])=[O:24].Cl>C1COCC1.CCCCCC>[CH2:1]([S:4][C:5]1[C:6]([S:10]([NH:13][C:14]([CH3:16])([CH3:15])[CH3:17])(=[O:12])=[O:11])=[C:7]([C:23]([OH:25])=[O:24])[S:8][CH:9]=1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 14254942HCID 14254942, compoundHCID 178418339Butyllithium

Product 1

HCID 14254943HCID 14254943, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 12.15 g 4-propylthio-3-N-(1,1-dimethylethyl)-3-thiophenesulfonamide in 150 mL THF was cooled to -30° C. and treated dropwise with 31.6 mL 2.69M n-butyllithium in hexane. The solution was warmed to 20° C. for 1.5 hours and then cooled to -80° C. 8.8 g Solid carbon dioxide was added in one portion, the mixture was warmed to 20° C. and poured over ice and hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated to a solid. The product was purified by recrystallization from butyl chloride to give 10.4 g of light yellow solid; m.p. 123°-126° C.

Workup

  1. temperaturecooled to -80° C
  2. temperaturethe mixture was warmed to 20° C.
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated to a solid
  8. customThe product was purified by recrystallization from butyl chloride

Sources & evidence

ORD record
ord-30f24c6710b9490f98017b21d1daf34a
Source dataset
uspto-grants-1988_05
Patent number
US04743290

Reaction notes

Loading…