Sodium hydride → HCID 21548301, compound

HRID 1605087Notes

Reaction equation

HRID 1605087 reaction equation
[H-].[Na+].[CH2:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:5][CH2:4]1>CN(C)C=O>[C:16]([N:14]1[C:15]2[CH2:3][CH2:4][CH2:5][CH:6]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[C:7]=2[C:8]2[C:13]1=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:17])[C:6]1[CH:7]=[CH:15][CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21548342HCID 21548342, compound

Product 1

HCID 21548301HCID 21548301, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 0.85 g. sodium hydride in 150 ml. of dry dimethylformamide was added, portionwise, 9 g. of benzyl 1,2,3,4-tetrahydrocarbazole-4-carboxylate. The mixture was heated on a steam bath for 15 minutes, the heat was removed, 4 ml. benzoyl chloride was added dropwise to the still hot mixture and heating was resumed for two hours. The mixture, after standing overnight at room temperature, was poured into water containing 4 ml. glacial acetic acid and the resulting mixture was extracted with ether. The ether extract was washed with sodium bicarbonate solution and water, dried, and evaporated to dryness. The resulting residue in 50 ml. dimethylformamide was again treated with 0.42 g. sodium hydride and 2 ml. benzoyl chloride and worked up as described above and the resulting crude product was chromatographed on a 45 mm. by 620 mm. silica gel column using as eluant hexane and hexane containing increasing amounts of ether. There was thus obtained with 7.5% ether in hexane, after evaporation to dryness and recrystallization, 4.6 g. of the title compound; m.p. 107°-109°C. (methyl alcohol).

Workup

  1. temperatureThe mixture was heated on a steam bath for 15 minutes
  2. customthe heat was removed
  3. additionbenzoyl chloride was added dropwise to the still hot mixture
  4. temperatureheating
  5. waitThe mixture, after standing overnight at room temperature
  6. additionwas poured into water containing 4 ml
  7. extractionglacial acetic acid and the resulting mixture was extracted with ether
  8. extractionThe ether extract
  9. washwas washed with sodium bicarbonate solution and water
  10. customdried
  11. customevaporated to dryness
  12. additiondimethylformamide was again treated with 0.42 g
  13. customwas chromatographed on a 45 mm
  14. temperatureincreasing amounts of ether
  15. customThere was thus obtained with 7.5% ether in hexane
  16. customafter evaporation
  17. customto dryness and recrystallization, 4.6 g

Sources & evidence

ORD record
ord-758763336e48432083f09544aa59c27d
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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