Sodium Chloride → HCID 86749894, compound

HRID 864072Notes

Reaction equation

HRID 864072 reaction equation
CS(Cl)(=O)=O.[CH2:6]([O:8][C:9]1[CH:24]=[C:23]2[C:12]([CH2:13][C:14]3[CH:18]=[N:17][N:16]([CH2:19][C@H:20](O)[CH3:21])[C:15]=32)=[CH:11][CH:10]=1)[CH3:7].C(N(CC)CC)C.[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[Na+]>ClCCl.CN(C)C=O>[N:32]([C@@H:20]([CH3:21])[CH2:19][N:16]1[C:15]2=[CH:23][C:24]3[C:13]([CH2:12][CH:11]=[CH:10][C:9]=3[O:8][CH2:6][CH3:7])=[C:14]2[CH:18]=[N:17]1)=[N+:33]=[N-:34]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 53798743HCID 53798743, compound

Product 1

HCID 86749894HCID 86749894, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.29 ml (3.79 mmol) of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0°, of 0.49 g (1.9 mmol) of (R)-1-(7-ethoxy-1,4-dihydro-indeno[1,2-c]pyrazol-1-yl)-propan-2-ol and 1.06 ml (7.6 mmol) of triethylamine in 30 ml of dichloromethane and the mixture was stirred at this temperature for a further 50 minutes. The reaction mixture was subsequently diluted with 100 ml of dichloromethane, washed twice with 50 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 50 ml of dichloromethane. The combined organic phases were washed with 70 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The yellowish solid obtained was dissolved in 25 ml of anhydrous dimethylformamide, treated with 0.25 g (3.8 mmol) of sodium azide and the reaction mixture was heated to 70° while stirring for 22 hours. After cooling, the solution was poured into 70 ml of semi-saturated sodium chloride solution and extracted twice with 70 mi of diethyl ether each time. The combined organic phases were washed once with 50 ml of water and once with 50 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The brown oil obtained was purified by column chromatography on silica gel (ethyl acetate). 0.53 g (99%) of (S)-1-(2-azido-propyl)-7-ethoxy-1,4-dihydro-indeno[2,1-c]pyrazole was obtained as a light yellow solid.

Workup

  1. stirringthe mixture was stirred at this temperature for a further 50 minutes
  2. washwashed twice with 50 ml of saturated sodium hydrogen carbonate solution each time
  3. extractionthe combined aqueous phases were extracted once with 50 ml of dichloromethane
  4. washThe combined organic phases were washed with 70 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in a vacuum
  7. customThe yellowish solid obtained
  8. temperaturethe reaction mixture was heated to 70°
  9. stirringwhile stirring for 22 hours
  10. temperatureAfter cooling
  11. extractionextracted twice with 70 mi of diethyl ether each time
  12. washThe combined organic phases were washed once with 50 ml of water and once with 50 ml of saturated sodium chloride solution
  13. dry with materialdried over magnesium sulfate
  14. concentrationthe solution was concentrated in a vacuum
  15. customThe brown oil obtained
  16. customwas purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-1e5311fe4ab34dd88bf3050d3fb825b9
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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