Sodium Azide → HCID 10703417, compound

HRID 2229147Notes

Reaction equation

HRID 2229147 reaction equation
N([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:7]=1.[N-:18]=[N+:19]=[N-].[Na+]>C(O)(C(F)(F)F)=O>[N:5]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=1)=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 10703417HCID 10703417, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Following the general procedure of Marchesini (J. Org. Chem. 49, p. 4287-4290, 1984), sodium nitrite (38 g, 0.56 mol) was slowly added to a stirred and cooled (0° C.) mixture of ethyl 4-aminophenylacetate (25 g, 0.14 mol) in 700 mL of TFA. After the addition was complete, the reaction was stirred at 0° C. for another 0.5 hour and then sodium azide (27 g, 0.42 mol) was slowly added over a period of 0.5 hours. The mixture was stirred for another 2 hours at 0° C. and then quenched with ice water and the product was extracted with EtOAc. The organic phase was washed with water, dried over magnesium sulfate, filtered, concentrated to yield 26.5 g (90%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ7.31 (d, J=8 Hz, 2H), 7.07 (d, J=7 Hz, 2H), 4.07 (q, J=7 Hz, 2H), 3.66 (s, 2H), 1.17 (t, J=7 Hz, 3H).

Workup

  1. additionwas slowly added to
  2. temperaturecooled
  3. additionAfter the addition
  4. stirringthe reaction was stirred at 0° C. for another 0.5 hour
  5. stirringThe mixture was stirred for another 2 hours at 0° C.
  6. customquenched with ice water
  7. extractionthe product was extracted with EtOAc
  8. washThe organic phase was washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-dd6c111677214937ad501c3defb46afa
Source dataset
uspto-grants-2002_07
Patent number
US06420349B1

Reaction notes

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