4-Fluorophenyl isocyanate → HCID 22936728, compound

HRID 387736Notes

Reaction equation

HRID 387736 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-4fdacf55c40c403cae3cab533b35e76c
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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