Ammonia → NSC686966

HRID 2229434Notes

Reaction equation

HRID 2229434 reaction equation
Br[C:2]1[C:3]([CH2:11][CH2:12][C:13]#[N:14])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.N.[N-]=[N+]=[N-].[Na+].[Na].[Cl-].[NH4+]>>[O:9]1[C:5]2[CH:4]=[C:3]3[CH2:11][CH:12]([C:13]#[N:14])[C:2]3=[CH:10][C:6]=2[O:7][CH2:8]1

Participants

6

Reactant 5

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 5360545SodiumHCID 18467755HCID 18467755, compound

Product 1

HCID 390052NSC686966

Procedure

46 g of 3-(6-bromo-1,3-benzodioxol-5-yl)propanenitrile are introduced in portions into 1.4 liters of liquid ammonia in which there is dissolved sodium azide which was prepared previously by the introduction of 16.7 g of sodium into the liquid ammonia. After 30 minutes' contact, the reaction mixture is treated with 38.7 g of ammonium chloride, and then the ammonia is distilled off at room temperature. The residue is taken up in ether and filtered; the precipitate is washed with ether. The combined ethereal phases are evaporated and the resulting residue is recrystallised from isopropyl alcohol, enabling the expected product to be isolated.

Workup

  1. distillationthe ammonia is distilled off at room temperature
  2. filtrationfiltered
  3. washthe precipitate is washed with ether
  4. customThe combined ethereal phases are evaporated
  5. customthe resulting residue is recrystallised from isopropyl alcohol
  6. customto be isolated

Sources & evidence

ORD record
ord-2fb5a13e849c4dc79aae508f0cdda203
Source dataset
uspto-grants-2002_07
Patent number
US06420413B2

Reaction notes

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