Benzenesulfonyl chloride → HCID 59637337, compound

HRID 1842868Notes

Reaction equation

HRID 1842868 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]#[N:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C.CCCCCC>ClCCl>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]([S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 178441039HCID 178441039, compound

Product 1

HCID 59637337HCID 59637337, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-tert-butyl-1H-pyrazole-5-carbonitrile (3 g, 20 mmol) in dichloromethane (30 ml, 10 times) TEA (2.44 g (3.36 ml), 24 mmol, 1.2 eq) was added at 0° C. Then phenylsulfonyl chloride (2.84 g (2 ml), 10 mmol, 0.8 eq) was added at 0° C. and the reaction mass was stirred for 12 h at room temperature. Progress of the reaction was monitored by TLC (20% ethyl acetate-hexane, Rf˜0.6). On completion of the reaction, ice water (20 ml) was added to reaction mixture, organic layer was separated and washed with 1N HCl (2×20 ml followed by with water (2×15 ml), Dried the contents over sodium sulfate, concentrated under reduced pressure and the crude product obtained was recrystallized from hexane to yield the required product as an off white solid (4 g, 68%).

Workup

  1. additionwas added to reaction mixture, organic layer
  2. customwas separated
  3. washwashed with 1N HCl (2×20 ml
  4. dry with materialDried the contents over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe crude product obtained
  7. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-b3b7b309d22a4890afff71b543710831
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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