Carbon Dioxide → HCID 18960410, compound

HRID 1707935Notes

Reaction equation

HRID 1707935 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[C:32](=[O:34])=[O:33].Cl>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:10]=1[C:32]([OH:34])=[O:33])(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 18960404HCID 18960404, compoundHCID 178418339Butyllithium

Product 1

HCID 18960410HCID 18960410, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of 1.8 g (4.7 mmol) of N-(1,1-dimethylethyl)-1-[2-(tetrahydro-2-pyranyloxy)-ethyl]-1H-indole-3-sulfonamide was dissolved in 30 mL anhydrous THF and cooled to -60° C. under nitrogen atmosphere. To this was added dropwise, with stirring, 8.0 mL (12.8 mmol) 1.6M butyllithium in hexanes and the mixture allowed to warm to 0° C. for 20 minutes then recooled to -60° C. A large excess of crushed dry ice (4 g CO2) was added all at once then the mixture was stirred overnight at ambient temperature. Hydrochloric acid (1N, 15 mL) plus ice was then added and the mixture extracted three times with ethyl acetate. The organic extracts were washed once with brine, dried (Na2SO4) and evaporated in vacuo. The solid residue was triturated and collected by filtration with n-butyl chloride and hexane to afford 1.80 g of the title compound, m.p. 149°-151° C. dec.

Workup

  1. additionTo this was added dropwise
  2. temperatureto warm to 0° C. for 20 minutes
  3. customthen recooled to -60° C
  4. stirringwas stirred overnight at ambient temperature
  5. extractionthe mixture extracted three times with ethyl acetate
  6. washThe organic extracts were washed once with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe solid residue was triturated
  10. filtrationcollected by filtration with n-butyl chloride and hexane

Sources & evidence

ORD record
ord-6aaa2bcd2d3e413aa4ae0c223660941a
Source dataset
uspto-grants-1994_10
Patent number
US05356862

Reaction notes

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