Sodium Chloride → HCID 19420931, compound

HRID 864047Notes

Reaction equation

HRID 864047 reaction equation
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]1[CH:19]=[CH:18][CH2:17][C:16]2[C:9]=1[CH:10]=[C:11]1[C:15]=2[C:14]([CH3:20])=[N:13][N:12]1[CH2:21][C@@H: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:12]1[C:11]2=[CH:10][C:9]3[C:16]([CH2:17][CH:18]=[CH:19][C:8]=3[O:7][CH3:6])=[C:15]2[C:14]([CH3:20])=[N:13]1)=[N+:33]=[N-:34]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 86749888HCID 86749888, compound

Product 1

HCID 19420931HCID 19420931, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.7 ml (8.52 mmol) of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0°, of 1.1 g (4.26 mmol) of (S)-1-(7-methoxy-3-methyl-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol and 2.4 ml (17 mmol) of triethylamine in 60 ml of dichloromethane and the mixture was stirred at this temperature for a further 1.5 hours. The reaction mixture was subsequently diluted with 130 ml of dichloromethane, washed twice with 60 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 brown oil obtained was dissolved in 60 ml of anhydrous dimethylformamide, treated with 0.55 g (8.46 mmol) of sodium azide and the reaction mixture was heated to 80° for 15 hours while stirring. After cooling, the solution was poured into 80 ml of semi-saturated sodium chloride solution and extracted twice with 80 ml of diethyl ether each time. The combined organic phases were washed once with 80 ml of water and once with 80 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 g (83%) of (RS)-1-(2-azido-propyl)-7-methoxy-3-methyl-1,4-dihydro-indeno[2,1-c]pyrazole was obtained as a dark brown oil.

Workup

  1. stirringthe mixture was stirred at this temperature for a further 1.5 hours
  2. washwashed twice with 60 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 brown oil obtained
  8. temperaturethe reaction mixture was heated to 80° for 15 hours
  9. stirringwhile stirring
  10. temperatureAfter cooling
  11. extractionextracted twice with 80 ml of diethyl ether each time
  12. washThe combined organic phases were washed once with 80 ml of water and once with 80 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/toluene 1:1)

Sources & evidence

ORD record
ord-712dd7cc909443d983813d4614d68761
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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