Benzoyl chloride → HCID 178434571, compound

HRID 719275Notes

Reaction equation

HRID 719275 reaction equation
[CH3:1][C:2]1[C:6]([NH2:7])=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][N:3]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:1][C:2]1[C:6]([NH:7][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:4][N:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178434570HCID 178434570, compound

Product 1

HCID 178434571HCID 178434571, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a rt solution of 550 mg of 3-methyl-5-phenyl-1H-pyrazol-4-ylamine (prepared in accordance with the procedure set forth in UK 2 185 255, Example 2A) in 8.5 mL pyridine was added 370 μL of benzoyl chloride. The reaction was stirred for 1 h and then concentrated under reduced pressure. The residue was dissolved in chloroform and washed with 0.5 N hydrochloric acid and then saturated aqueous sodium carbonate. The organic portion was dried with sodium sulfate and concentrated under reduced pressure and purified by means of MPLC (12 g SiO2, 40% ethyl acetate:heptane) to give the title compound as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with 0.5 N hydrochloric acid
  4. dry with materialThe organic portion was dried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by means of MPLC (12 g SiO2, 40% ethyl acetate:heptane)

Sources & evidence

ORD record
ord-0eb3d4382cd345abae15653fc996d42f
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Reaction notes

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