4-Toluenesulfonyl chloride → HCID 561427, compound

HRID 1686272Notes

Reaction equation

HRID 1686272 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:9])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 163764-nitro-1H-pyrazole

Product 1

HCID 561427HCID 561427, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-nitro-1H-pyrazole (500 mg, 4.4 mmol), 4-methylbenzene-1-sulfonyl chloride (840 mg, 4.4 mmol), and triethylamine (510 mg, 5 mmol) were stirred in DMF (25 mL) at 80° C. for 1 hour. The reaction was cooled, diluted with H2O (200 mL) and extracted with ethyl acetate (3×, 100 ml). The organic phase was washed with aqueous 1N HCl (200 mL) and H2O (200 mL), dried over sodium sulfate, filtered and concentrated on the rotovap. The solid was triturated with hexanes to afford 4-nitro-1-tosyl-1H-pyrazole (600 mg, 50%) as an off white solid. 1H NMR (DMSO-d6, 400 MHz), 2.40 (s, 3H), 7.52 (d, 2H, J=8.4 Hz), 7.98 (d, 2H, J=8.8 Hz), 8.57 (s, 1H), 9.58 (s, 1H).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (3×, 100 ml)
  3. washThe organic phase was washed with aqueous 1N HCl (200 mL) and H2O (200 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on the rotovap
  7. customThe solid was triturated with hexanes

Sources & evidence

ORD record
ord-5115dd045e104477aa9ca38da98efc9c
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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