Thionyl Chloride → HCID 15886915, compound

HRID 850741Notes

Reaction equation

HRID 850741 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:22]=[C:21]([CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[C:20](=[O:30])[C:8]4[CH:9]=[C:10]([O:15][CH2:16][C:17]([OH:19])=[O:18])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.S(Cl)(Cl)=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:22]=[C:21]([CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[C:20](=[O:30])[C:8]4[CH:9]=[C:10]([O:15][CH2:16][C:17]([O:19][CH2:13][CH2:14][CH2:2][CH2:3][CH3:4])=[O:18])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15886913HCID 15886913, compound

Product 1

HCID 15886915HCID 15886915, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10-bromo-2-carboxymethyloxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (300 mg) obtained in Example 6 was suspended in anhydrous benzene (10 ml), and to the suspension was added thionyl chloride (0.95 ml) at room temperature. The mixture was heated under reflux in an argon atmosphere for 3 hours and allowed to cool. The solvent was evaporated under reduced pressure, and after adding anhydrous benzene (5 ml), the solvent was evaporated again. The resulting residue was dissolved in anhydrous methylene chloride (3 ml), and the solution was added dropwise to a solution of 1-pentanol (0.065 ml) and triethylamine (0.18 ml) dissolved in methylene chloride (30 ml) in an ice bath, and the solution was stirred for 20 minutes. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride. The methylene chloride layer was repeatedly washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The residual crude crystals were washed with ether, and recovered by filtration to obtain the title compound (200 mg, 58%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an argon atmosphere for 3 hours
  3. temperatureto cool
  4. customThe solvent was evaporated under reduced pressure
  5. additionafter adding anhydrous benzene (5 ml)
  6. customthe solvent was evaporated again
  7. dissolutionThe resulting residue was dissolved in anhydrous methylene chloride (3 ml)
  8. additionthe solution was added dropwise to a solution of 1-pentanol (0.065 ml) and triethylamine (0.18 ml)
  9. dissolutiondissolved in methylene chloride (30 ml) in an ice bath
  10. additionWater was added to the reaction mixture
  11. extractionthe mixture was extracted with methylene chloride
  12. washThe methylene chloride layer was repeatedly washed with saturated aqueous solution of sodium chloride
  13. dry with materialdried over anhydrous sodium sulfate
  14. washThe residual crude crystals were washed with ether
  15. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-486256fcb9fe4bf8ac1012b449e07f37
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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