Triethylamine → HCID 19036452, compound

HRID 264576Notes

Reaction equation

HRID 264576 reaction equation
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:22](=[CH:23][CH:24]=1)[C:13]1[N:14]([CH2:18][CH:19](O)[CH3:20])[C:15]([CH3:17])=[CH:16][C:12]=1[CH2:11]2.C(N(CC)CC)C.[N-:32]=[N+:33]=[N-:34].[Na+]>ClCCl.CN(C)C=O.O>[N:32]([CH:19]([CH3:20])[CH2:18][N:14]1[C:15]([CH3:17])=[CH:16][C:12]2[CH2:11][C:10]3[C:22]([C:13]1=2)=[CH:23][CH:24]=[C:8]([O:7][CH3:6])[CH:9]=3)=[N+:33]=[N-:34]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 19036546HCID 19036546, compound

Product 1

HCID 19036452HCID 19036452, compoundYield 67.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

0.7 ml of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0°, of 1.16 g of (RS)-1-(6-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 2.5 ml of triethylamine in 50 ml of dichloromethane and the solution was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently added to 70 ml of water, extracted twice with 100 ml of dichloromethane each time and the combined organic phases were washed once with 70 ml of saturated sodium hydrogen carbonate solution and once with 70 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The brown oil obtained was dissolved in 40 ml of anhydrous dimethylformamide, treated with 0.58 g of sodium azide and the reaction mixture was heated to 80° while stirring for 16 hours. After cooling the solution was poured into 70 ml of water and extracted twice with 100 ml of ethyl acetate each time. The combined organic phases were washed once with 70 ml of water and once with 70 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 (toluene). 0.86 g (55%) of (RS)-1-(2-azido-propyl)-6-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrole was obtained as a colorless oil.

Workup

  1. stirringthe solution was stirred at this temperature for an additional 1.5 hours
  2. extractionextracted twice with 100 ml of dichloromethane each time
  3. washthe combined organic phases were washed once with 70 ml of saturated sodium hydrogen carbonate solution and once with 70 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in a vacuum
  6. customThe brown oil obtained
  7. temperaturethe reaction mixture was heated to 80°
  8. stirringwhile stirring for 16 hours
  9. temperatureAfter cooling the solution
  10. extractionextracted twice with 100 ml of ethyl acetate each time
  11. washThe combined organic phases were washed once with 70 ml of water and once with 70 ml of saturated sodium chloride solution
  12. dry with materialdried over magnesium sulfate
  13. concentrationthe solution was concentrated in a vacuum
  14. customThe brown oil obtained
  15. customwas purified by column chromatography on silica gel (toluene)

Sources & evidence

ORD record
ord-1f2dcf789eb64746a3168b225d080903
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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