Benzyl Bromide → HCID 54120306, compound

HRID 465990Notes

Reaction equation

HRID 465990 reaction equation
C(N(CC)C(C)C)(C)C.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+:18]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)([O-:20])=[O:19]>C(#N)C>[CH2:10]([N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]1=[N:21][N+:18]([O-:20])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 33520N-Pyridin-2-ylnitramideHCID 81531Diisopropylethylamine

Product 1

HCID 54120306HCID 54120306, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

20 ml (0.114 mole) of N,N-diisopropylethylamine and 12 ml (0.1 mole) of benzyl bromide are added to a suspension containing 14 g (0.1 mole) of 2-(nitroamino)pyridine [prepared according to J. Am. Chem. Soc. 77, 3154 (1955)] in 100 ml of acetonitrile, then the mixture is refluxed for 2.5 hours. The reaction mixture is cooled down then evaporated under reduced pressure, the residue is triturated with water, the suspension obtained is filtered and washed with a great volume of water. The filter cake is thoroughly sucked, then suspended in 50 ml of petroleum ether, filtered and washed again with petroleum ether to give 14.2 g (62%) of the named product, m.p.: 125°-126° C. (recrystallized from ethyl acetate).

Workup

  1. temperaturethe mixture is refluxed for 2.5 hours
  2. temperatureThe reaction mixture is cooled down
  3. customthen evaporated under reduced pressure
  4. customthe residue is triturated with water
  5. customthe suspension obtained
  6. filtrationis filtered
  7. washwashed with a great volume of water
  8. filtrationfiltered
  9. washwashed again with petroleum ether
  10. customto give
  11. custom14.2 g (62%) of the named product, m.p.: 125°-126° C. (recrystallized from ethyl acetate)

Sources & evidence

ORD record
ord-76d4f1361c144826bd13e58cdfd8cd6d
Source dataset
uspto-grants-1992_10
Patent number
US05155123

Reaction notes

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