Sodium Chloride → HCID 19420916, compound

HRID 864060Notes

Reaction equation

HRID 864060 reaction equation
CS(Cl)(=O)=O.[CH2:6]([O:8][C:9]1[CH:20]=[CH:19][CH2:18][C:17]2[C:10]=1[CH:11]=[C:12]1[C:16]=2[CH:15]=[N:14][N:13]1[CH2:21][CH:22](O)[CH3:23])[CH3:7].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:13]1[C:12]2=[CH:11][C:10]3[C:17]([CH2:18][CH:19]=[CH:20][C:9]=3[O:8][CH2:6][CH3:7])=[C:16]2[CH:15]=[N:14]1)=[N+:33]=[N-:34]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 19420954HCID 19420954, compound

Product 1

HCID 19420916HCID 19420916, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.2 ml (15.5 mmol) of methanesulfonyl chloride were added dropwise while stirring to a solution, cooled to 0°, of 2 g (7.7 mmol) of (RS)-1-(7-ethoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol and 4.3 ml (31 mmol) of triethylamine in 50 ml of dichloromethane and the mixture was stirred at this temperature for a further 50 minutes. The reaction mixture was subsequently diluted with 130 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 50 ml of anhydrous dimethylformamide, treated with 1 g (15.5 mmol) of sodium azide and the reaction mixture was heated to 75° for 15 hours while stirring. After cooling the solution was poured into 80 ml of semi-saturated sodium chloride solution and extracted twice with 100 ml of diethyl ether each time. The is 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). 2.06 g (94%) of (RS)-1-(2-azido-propyl)-7-ethoxy-1,4-dihydro-indeno[2,1-c]pyrazole were obtained as a light yellow oil.

Workup

  1. stirringthe mixture was stirred at this temperature for a further 50 minutes
  2. washwashed twice with 70 ml of saturated sodium hydrogen carbonate solution each time
  3. extractionthe combined aqueous phases were extracted once with 70 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 yellow oil obtained
  8. temperaturethe reaction mixture was heated to 75° for 15 hours
  9. stirringwhile stirring
  10. temperatureAfter cooling the solution
  11. extractionextracted twice with 100 ml of diethyl ether each time
  12. washwere 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)

Sources & evidence

ORD record
ord-806b68d8581349388c61b892f2f14a47
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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