Sodium Chloride → HCID 19420927, compound

HRID 864058Notes

Reaction equation

HRID 864058 reaction equation
CS(Cl)(=O)=O.[F:6][C:7]1[CH:18]=[CH:17][C:16]([CH3:20])([CH3:19])[C:15]2[C:8]=1[CH:9]=[C:10]1[C:14]=2[CH:13]=[N:12][N:11]1[CH2:21][CH:22](O)[CH3:23].C(N(CC)CC)C.[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[Na+]>ClCCl.CN(C)C=O>[N:32]([CH:22]([CH3:23])[CH2:21][N:11]1[C:10]2=[CH:9][C:8]3[C:15]([C:16]([CH3:20])([CH3:19])[CH:17]=[CH:18][C:7]=3[F:6])=[C:14]2[CH:13]=[N:12]1)=[N+:33]=[N-:34]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 19420914HCID 19420914, compound

Product 1

HCID 19420927HCID 19420927, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

1 ml (13 mmol) of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0°, of 1.7 g (6.5 mmol) of (RS)-1-(7-fluoro-4,4-dimethyl-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol and 3.6 ml (26 mmol) of triethylamine in 60 ml of dichloromethane and the mixture was stirred at this temperature for a further 1.5 hours. The reaction S mixture was subsequently diluted with 150 ml of dichloromethane, washed twice with 70 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 70 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 yellow oil obtained was dissolved in 40 ml of anhydrous dimethylformamide, treated with 0.85 g (13 mmol) of sodium azide and the reaction mixture was heated to 70° for 15 hours while stirring. After cooling, the solution was poured into 100 ml of semi-saturated sodium chloride solution and extracted twice with 100 ml of diethyl ether each time. The combined organic phases were washed once with 100 ml of water and once with 100 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/toluene 1:1). 1.66 g (90%) of (RS)-1-(2-azido-propyl)-7-fluoro-4,4-dimethyl-1,4-dihydro-indeno[2,1-c]pyrazole were obtained as a yellow oil.

Workup

  1. stirringthe mixture was stirred at this temperature for a further 1.5 hours
  2. customThe reaction S mixture
  3. washwashed twice with 70 ml of saturated sodium hydrogen carbonate solution each time
  4. extractionthe combined aqueous phases were extracted once with 70 ml of dichloromethane
  5. washThe combined organic phases were washed with 70 ml of saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in a vacuum
  8. customThe yellow oil obtained
  9. temperaturethe reaction mixture was heated to 70° for 15 hours
  10. stirringwhile stirring
  11. temperatureAfter cooling
  12. extractionextracted twice with 100 ml of diethyl ether each time
  13. washThe combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution
  14. dry with materialdried over magnesium sulfate
  15. concentrationthe solution was concentrated in a vacuum
  16. customThe brown oil obtained
  17. customwas purified by column chromatography on silica gel (ethyl acetate/toluene 1:1)

Sources & evidence

ORD record
ord-9e762ff2cecf4a82b26c3f6981bc08a1
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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