Pyridine → HCID 57743007, compound

HRID 1924231Notes

Reaction equation

HRID 1924231 reaction equation
[I:1][C:2]1[C:3]([CH3:8])=[N:4][NH:5][C:6]=1[CH3:7].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.N1C=CC=CC=1>C(Cl)Cl>[I:1][C:2]1[C:3]([CH3:8])=[N:4][N:5]([S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:9])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 971153,5-Dimethyl-4-iodo-1H-pyrazole

Product 1

HCID 57743007HCID 57743007, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 ml reaction vessel under argon, a solution of crude 4-iodo-3,5-dimethyl-1H-pyrazole x52 (1.15 g, 5.2 mmol) in 25 ml of dry CH2Cl2 is added to 4-methylbenzenesulfonyl chloride (1.18 g, 6.2 mmol). Pyridine (0.42 ml, 5.2 mmol) is added and the mixture is stirred for 16 h at room temperature. The organic phase is washed with water, dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography on silicagel (CH2Cl2/hexane: 70/30 (v/v)) to afford 4-iodo-3,5-dimethyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole x53 (1.44 g).

Workup

  1. customIn a 50 ml reaction vessel under argon
  2. washThe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography on silicagel (CH2Cl2/hexane: 70/30 (v/v))

Sources & evidence

ORD record
ord-73e79a982d544b5a95bda75f5060f1e3
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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