Benzylamine → HCID 10800431, compound

HRID 1955113Notes

Reaction equation

HRID 1955113 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C(N(CC)C(C)C)(C)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:21]([NH:28][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[F:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 10800431HCID 10800431, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 23.9 g(16.9 mL, 0.15mol) of 3,4-difluoronitrobenzene and 29.1 g(39.2 mL, 0.23 mol) of N,N-diisopropylethylamine in 285 mL acetonitrile was treated with 19.3 g(19.7 mL, 0.18 mol) of benzylamine, followed by warming at reflux for 5 h. The mixture was concentrated in vacuo and the residue was dissolved in 200 mL ethyl acetate, followed by extraction with water (3×50 mL). Drying (Na2SO4) and concentration in vacuo afforded a yellow solid, which was recrystallized from hot ethyl acetate-hexane to afford 32.25 g(87%) of the title compound as yellow-orange needles, mp 97.5-99° C.

Workup

  1. temperatureby warming
  2. temperatureat reflux for 5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in 200 mL ethyl acetate
  5. extractionfollowed by extraction with water (3×50 mL)
  6. customDrying
  7. concentration(Na2SO4) and concentration in vacuo
  8. customafforded a yellow solid, which
  9. customwas recrystallized from hot ethyl acetate-hexane

Sources & evidence

ORD record
ord-f4d8ae103f0443b3940b2fb270e6a79e
Source dataset
uspto-grants-2000_09
Patent number
US06124334

Reaction notes

Loading…