4-Fluorophenyl isocyanate → HCID 22936728, compound

HRID 853258Notes

Reaction equation

HRID 853258 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[O:13][C:14]2[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>C(OCC)(=O)C>[C:1]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[O:13][C:14]2[CH:15]=[CH:16][C:17]([NH:18][C:29]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=3)=[O:30])=[CH:19][CH:20]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 22936276HCID 22936276, compound

Product 1

HCID 22936728HCID 22936728, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate (10 ml) was added to 4-(3-phenylpyridin-4-yl)oxyaniline (84 mg, 0.32 mM), and then parafluorophenyl isocyanate (0.54 ml, 4.7 mM) was added while stirring, which was continued for 40 minutes. After adding NH type silica gel to the reaction solution, the solvent was distilled off under reduced pressure to adsorb the reaction product onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, for column purification (chloroform:methanol=10:1). After adding ethyl acetate and n-hexane to the obtained residue, the solvent was distilled off under reduced pressure to obtain the target compound (82 mg) as a light yellow amorphous substance.

Workup

  1. additionAfter adding NH type silica gel to the reaction solution
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe silica gel was charged into a dry column
  4. custompacked with NH type silica gel, for column purification (chloroform:methanol=10:1)
  5. additionAfter adding ethyl acetate and n-hexane to the obtained residue
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3a6d4aa5f80e46cebc07ebc59d824dc9
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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