Benzenesulfonyl chloride → HCID 59637337, compound

HRID 2271422Notes

Reaction equation

HRID 2271422 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 00° C. Then phenylsulfonyl chloride (2.84 g (2 ml), 10 mmol, 0.8 eq) was added at 00° 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 obtained was recrystallised 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 obtained
  7. customwas recrystallised from hexane

Sources & evidence

ORD record
ord-fb2de87519fc40789d22a8e75b9faad1
Source dataset
uspto-grants-2015_09
Patent number
US09120756B2

Reaction notes

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