Benzoyl chloride → (4-Iodo-1H-pyrazol-1-yl)(phenyl)methanone

HRID 2191079Notes

Reaction equation

HRID 2191079 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C(N(CC)CC)C.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[C:14]([N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 770224-Iodopyrazole

Product 1

HCID 14041588(4-Iodo-1H-pyrazol-1-yl)(phenyl)methanoneYield 87.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 4-iodopyrazole (10.30 g, 53.1 mmol) in toluene (50 mL) at r.t. was added triethylamine (8.10 mL, 58.1 mmol), followed by benzoyl chloride (8.20 g, 58.3 mmol). The reaction mixture was then heated to 100° C. and stirred for 4 h. The solid was filtered and washed with toluene (50 mL). The organic filtrate was diluted with EtOAc (100 mL), washed with water (3×50 ml), then brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo. Recrystallisation from hexanes gave the title compound (13.80 g, 87%) as a white solid. δH (DMSO-d6) 8.77 (1H, s), 8.05 (1H, s), 8.02-7.95 (2H, m), 7.74-7.67 (1H, m), 7.61-7.53 (2H, m).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with toluene (50 mL)
  3. additionThe organic filtrate was diluted with EtOAc (100 mL)
  4. washwashed with water (3×50 ml)
  5. dry with materialbrine (50 mL), dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customRecrystallisation from hexanes

Sources & evidence

ORD record
ord-196af8cfe582429b8cfa9df661d1db0f
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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