2,5-Dimethylaniline → n-(2,5-Dimethylphenyl)-n-{4-[2-(4-fluorophenyl)-2-oxoethyl]phenyl}urea

HRID 1371022Notes

Reaction equation

HRID 1371022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH2:9][C:10]2[CH:18]=[CH:17][C:13](C(O)=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CN(C1C2C([N:33]([CH3:35])C)=CC=CC=2C=CC=1)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.[CH3:53][C:54]1[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][C:55]=1[NH2:56]>C(#N)C>[CH3:53][C:54]1[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][C:55]=1[N:56]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:19])=[CH:18][CH:17]=1)[C:35]([NH2:33])=[O:43]

Participants

6

Reactant 4

HCID 72592,5-DimethylanilineHCID 88675Proton spongeHCID 199401P,P-Diphenylphosphinic azideHCID 185102554-[2-(4-Fluorophenyl)-2-oxoethyl]benzoic acid

Product 1

HCID 18510233n-(2,5-Dimethylphenyl)-n-{4-[2-(4-fluorophenyl)-2-oxoethyl]phenyl}urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoic acid (0.100 g, 0.387 mmol) in acetonitrile was added proton sponge ((0.083 g) and diphenylphosphoryl azide (0.106 g). The reaction mixture was refluxed for 30 minutes. 2,5-dimethyl aniline (0.047 g, 0.388 mmol) was added and the mixture was refluxed another 30 minutes. The reaction was quenched with HCl 1 M and extracted with ethyl acetate, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified using flash chromatography eluting with hexane/ethyl acetate 40% to give (0.052 g) of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. temperaturethe mixture was refluxed another 30 minutes
  3. customThe reaction was quenched with HCl 1 M
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified
  9. washeluting with hexane/ethyl acetate 40%

Sources & evidence

ORD record
ord-72d4cbd6606a4cda93c73c9c3908ad8e
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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