Sodium Azide → HCID 58056181, compound

HRID 1773594Notes

Reaction equation

HRID 1773594 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([CH:13](OS(C)(=O)=O)[CH3:14])[CH2:9]2)=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.ClC1C=CC(N2CCC(C(OS(C3C=CC(C)=CC=3)(=O)=O)C)C2)=C([N+]([O-])=O)C=1.[N-:51]=[N+:52]=[N-:53].[Na+]>CN(C)C=O.O>[N:51]([CH:13]([CH:10]1[CH2:11][CH2:12][N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[N+:20]([O-:22])=[O:21])[CH2:9]1)[CH3:14])=[N+:52]=[N-:53]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 58056180HCID 58056180, compoundHCID 86661372HCID 86661372, compound

Product 1

HCID 58056181HCID 58056181, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methanesulfonic acid 1-[1-(4-chloro-2-nitro-phenyl)-pyrrolidin-3-yl]-ethyl ester (285.9 mg), toluene-4-sulfonic acid 1-[1-(4-chloro-2-nitro-phenyl)-pyrrolidin-3-yl]-ethyl ester (55.2 mg) and sodium azide (185 mg) in N,N-dimethylformamide (ca. 5 mL) was heated at 80° C. overnight. The reaction mixture was cooled, diluted with water and extracted 3 times with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 90/10) to give 214 mg (76% yield) of 3-(1-azido-ethyl)-1-(4-chloro-2-nitro-phenyl)-pyrrolidine.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted 3 times with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 90/10)

Sources & evidence

ORD record
ord-4daa46c466314c57aaae3195cc50c178
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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