1-Fluoro-2-nitrobenzene → HCID 19809395, compound

HRID 345000Notes

Reaction equation

HRID 345000 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[N:11]1([CH2:17][C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(CC)C(C)C)(C)C>C(#N)C>[N:11]1([CH2:17][C:18]2[N:22]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N+:8]([O-:10])=[O:9])[CH:21]=[CH:20][N:19]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 2722464-(1H-imidazol-2-ylmethyl)morpholine

Product 1

HCID 19809395HCID 19809395, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 10 g of 2-fluoronitrobenzene, 13 g of 2-((4-morpholinyl)methyl)-imidazole, 18 mL of N,N-diisopropyl ethylamine, and 150 mL of acetonitrile, and heat at reflux for 48 hr. Remove the solvent under vacuum, and dissolve the residue in 500 mL of 2N H2SO4. Wash the aqueous portion with 400 mL of ether, basify with K2CO3, and extract with two 400 mL portions of CH2Cl2. Combine extracts, dry over MgSO4, charcoal treat and remove the solvent under vacuum to provide the title compound.

Workup

  1. temperatureat reflux for 48 hr
  2. customRemove the solvent under vacuum
  3. dissolutiondissolve the residue in 500 mL of 2N H2SO4
  4. washWash the aqueous portion with 400 mL of ether
  5. extractionextract with two 400 mL portions of CH2Cl2
  6. dry with materialCombine extracts, dry over MgSO4, charcoal
  7. additiontreat
  8. customremove the solvent under vacuum

Sources & evidence

ORD record
ord-277bbfb458bd45cc9b91d0dc82f80c5c
Source dataset
uspto-grants-1991_10
Patent number
US05055465

Reaction notes

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