Carbon Dioxide → HCID 9828906, compound

HRID 1955148Notes

Reaction equation

HRID 1955148 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)=[CH:16][C:4]=1[O:5][CH:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]([OH:9])=O)#[N:2].C(=O)=O.[CH:30]([C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1)([CH3:32])[CH3:31].[H-].[Na+]>ClCCl.CN(C)C=O>[C:1]([C:3]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)=[CH:16][C:4]=1[O:5][CH:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]([NH:42][S:39]([C:36]1[CH:37]=[CH:38][C:33]([CH:30]([CH3:32])[CH3:31])=[CH:34][CH:35]=1)(=[O:40])=[O:41])=[O:9])#[N:2]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 24758Sodium hydrideHCID 2323144-(1-Methylethyl)benzenesulfonamideHCID 9863916HCID 9863916, compound

Product 1

HCID 9828906HCID 9828906, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 2 (0.73 g) in dry dichloromethane (50 ml) was treated with N,N' carbonyldiimidazole (0.36 g) and stirred at 25° C. for 2 hours, when evolution of carbon dioxide was complete. A solution of 4-isopropylbenzenesulphonamide (0.60 g) in dry dimethylformamide (20 ml) was treated with sodium hydride (0.13 g, 60% dispersion in mineral oil) and stirred at 25° C. for 2 hours. This solution was then treated dropwise with the solution of acylimidazole prepared above and stirring was continued at 25° C. for 8 hours. The reaction mixture was evaporated, the residue diluted with water (50 ml) and extracted twice with ethyl acetate. The extracts were washed with water, dried and evaporated to give an orange oil which was purified by flash chromatography on silica eluting with ether. Fractions homogenous in the required product were combined and evaporated. The residual pale yellow solid (0.35 g) was recrystallized from a mixture of ethyl acetate and pentane affording the title compound (0.20 g) as colourless crystals, m.p. 187-189° C. [Elemental analysis:-C,63.7; H,4.79; N,5.12%. Calculated:-C,63.7; H,5.17; N,5.17%].

Workup

  1. stirringstirred at 25° C. for 2 hours
  2. customprepared above and
  3. stirringstirring
  4. waitwas continued at 25° C. for 8 hours
  5. customThe reaction mixture was evaporated
  6. additionthe residue diluted with water (50 ml)
  7. extractionextracted twice with ethyl acetate
  8. washThe extracts were washed with water
  9. customdried
  10. customevaporated
  11. customto give an orange oil which
  12. customwas purified by flash chromatography on silica eluting with ether
  13. customevaporated
  14. customThe residual pale yellow solid (0.35 g) was recrystallized from a mixture of ethyl acetate and pentane affording the title compound (0.20 g) as colourless crystals, m.p. 187-189° C. [Elemental analysis:-C,63.7; H,4.79; N,5.12%. Calculated:-C,63.7; H,5.17; N,5.17%]

Sources & evidence

ORD record
ord-7dc41ff37ab24bc790d5147f19322176
Source dataset
uspto-grants-2000_09
Patent number
US06124343

Reaction notes

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