Styrene-4-sulfonyl chloride → N-(5-isopropylpyridin-2-yl)-4-vinylbenzenesulfonamide

HRID 594141Notes

Reaction equation

HRID 594141 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)([CH3:3])[CH3:2].[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)=[CH2:12]>N1C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH:11]=[CH2:12])=[CH:14][CH:15]=2)(=[O:21])=[O:20])=[N:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9855777Styrene-4-sulfonyl chlorideHCID 179858055-(Propan-2-yl)pyridin-2-amine

Product 1

HCID 89876040N-(5-isopropylpyridin-2-yl)-4-vinylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-isopropylpyridin-2-amine (400 mg, 2.94 mmol) in pyridine (5 mL), stirred at room temperature, was added 4-vinylbenzene-1-sulfonyl chloride (760 mg, 3.75 mmol). The reaction mixture was stirred for 30 minutes then stood overnight. The solvent was evaporated in vacuo and the crude sample purified by normal phase chromatography on silica (Si) (0-50% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title product, 670 mg, as an off-white solid. LCMS (2 min, formic) Rt 0.98 min, m/z (ES+) 303 (M+H).

Workup

  1. waitthen stood overnight
  2. customThe solvent was evaporated in vacuo
  3. customthe crude sample purified by normal phase chromatography on silica (Si) (0-50% ethyl acetate-cyclohexane gradient)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-01faa48f2f634de2a97d950c83df31df
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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