4-Toluenesulfonyl chloride → HCID 12460282, compound

HRID 898787Notes

Reaction equation

HRID 898787 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][CH2:9][OH:10])[N:3]=1.C(N(CC)CC)C.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>CC#N>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:10][CH2:9][CH2:8][N:4]2[C:5]([CH3:7])=[CH:6][C:2]([CH3:1])=[N:3]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2596652-(3,5-Dimethyl-1H-pyrazol-1-yl)ethan-1-ol

Product 1

HCID 12460282HCID 12460282, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A cooled (0° C.) mixture of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-ethanol (0.48 g, 3.4 mmol) and triethylamine (0.47 mL, 3.4 mmol) in MeCN (5 mL) was treated with 4-methylbenzenesulfonyl chloride (0.72 g, 3.8 mmol), after which the mixture was kept cool in a refrigerator for 2 days. The mixture was then concentrated in vacuo to give a residue which was purified by chromatography on silica gel, eluting with ethyl acetate:hexane (1:1), to give 0.46 g (46%) of the title compound.

Workup

  1. temperatureA cooled
  2. temperatureafter which the mixture was kept cool in a refrigerator for 2 days
  3. concentrationThe mixture was then concentrated in vacuo
  4. customto give a residue which
  5. customwas purified by chromatography on silica gel
  6. washeluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record
ord-8303aa80d8cf49fc8d6fc1bba49bf482
Source dataset
uspto-grants-2008_04
Patent number
US07351821B2

Reaction notes

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