Ethyl Acetate → HCID 22250895, compound

HRID 890375Notes

Reaction equation

HRID 890375 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[O:9])=[CH:4][CH:3]=1.[N-:21]=[N+:22]=[N-:23].[Na+].C(OCC)(=O)C>CS(C)=O>[N:21]([C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[O:9])=[CH:4][CH:3]=1)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 22250915HCID 22250915, compound

Product 1

HCID 22250895HCID 22250895, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-N-[2-(2,4-dichlorophenyl)ethyl]pyridine-3-carboxamide (1 equivalent) and sodium azide (2.6 equivalents) were suspended in anhydrous DMSO (0.6 M) under nitrogen. The mixture was heated at 100° C. for four days. Ethyl acetate was added and the organic phase washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated to dryness and the resultant residue dissolved in a 1:1 ethyl acetate/DCM mixture. This solution was purified by flash chromatography over silica (1:1 ethyl acetate/DCM). The fractions coeluting with the major band (Rf 0.53, eluent: 1:1 ethyl acetate/DCM) were combined and evaporated to dryness. The residue was recrystallized from acetonitrile to give 6-azido-N-[2-(2,4-dichlorophenyl)ethyl]-pyrid ine-3-carboxamide as pale yellow needles. LCMS (MH+) 336.

Workup

  1. washthe organic phase washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. dissolutionthe resultant residue dissolved in a 1:1 ethyl acetate/DCM mixture
  6. customThis solution was purified by flash chromatography over silica (1:1 ethyl acetate/DCM)
  7. customevaporated to dryness
  8. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-11965ed1adf24ba3abca4725676cd1f5
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Reaction notes

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