Phenyl isocyanate → HCID 18674015, compound

HRID 1635932Notes

Reaction equation

HRID 1635932 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:3]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C1C=CC=CN=1)C>ClCCl>[F:14][C:11]1[CH:10]=[CH:9][C:8]([C:4]2[C:3]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:2]([NH:1][C:28]([NH:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:29])[N:6]([CH3:7])[N:5]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 218852-DimethylaminopyridineHCID 18674213HCID 18674213, compound

Product 1

HCID 18674015HCID 18674015, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg of 5-amino-3-(4-fluorophenyl)-1-methyl-4-(4-pyridyl)pyrazole was dissolved in 5 ml of dichloromethane. Then, 80 mg of phenyl isocyanate and 80 mg of dimethylaminopyridine were added thereto, followed by stirring at room temperature overnight. After the reaction mixture was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography using 20 g of silica gel and eluted with chloroform-methanol (50:1). Thus, 70 mg of the title compound was obtained and crystallized from ether.

Workup

  1. washAfter the reaction mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by column chromatography
  5. washeluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-b152e88d2b5246c8b68f3aeddb1e972c
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

Loading…