Dichloromethane → HCID 86753140, compound

HRID 2394454Notes

Reaction equation

HRID 2394454 reaction equation
C(Cl)[Cl:2].O[CH:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6][N:7]1[C:15]2[C:10](=[C:11]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.C(N(CC)CC)C.CS(Cl)(=O)=O>C(OCC)(=O)C>[Cl:2][CH:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6][N:7]1[C:15]2[C:10](=[C:11]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86753139HCID 86753139, compound

Product 1

HCID 86753140HCID 86753140, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 10 ml of methylene chloride, there were dissolved 150 mg of 5-[1-(2-hydroxy-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione prepared in Example 323 and 45 mg of triethylamine under an argon gas atmosphere and then 51 mg of methanesulfonyl chloride was added to the solution under ice-cooling. After stirring at room temperature for 30 minutes, 30 ml of ethyl acetate was added to the solution, the mixture was in order washed with a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and then the solvent was removed by evaporation under reduced pressure. The resulting residue was dissolved in 10 ml of dimethylformamide, followed by addition of 21 mg of lithium chloride and heating to 70° C. with stirring for 20 hours. The solution was poured into a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (20 ml×3). The resulting extract was in order washed with a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give a crude product. The product was purified by preparatory silica gel thin layer chromatography (hexane:ethyl acetate=10:1) to give 35 mg of 5-[1-(2-chloro-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione as a yellow amorphous substance. The yield thereof was found to be 22%.

Workup

  1. temperaturecooling
  2. washwashed with a 10% citric acid aqueous solution
  3. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate
  4. customthe solvent was removed by evaporation under reduced pressure
  5. dissolutionThe resulting residue was dissolved in 10 ml of dimethylformamide
  6. additionfollowed by addition of 21 mg of lithium chloride
  7. temperatureheating to 70° C.
  8. stirringwith stirring for 20 hours
  9. additionThe solution was poured into a 10% ammonium chloride aqueous solution
  10. extractionextracted with ethyl acetate (20 ml×3)
  11. extractionThe resulting extract
  12. washwashed with a 10% citric acid aqueous solution
  13. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate
  14. customthe solvent was removed through evaporation under reduced pressure
  15. customto give a crude product
  16. customThe product was purified by preparatory silica gel thin layer chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2627c31a3c6148989c2abb94605d9a71
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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