Hydroquinone → 4-Ethenyl-N-(3-methyl-2-pyridinyl)benzenesulfonamide

HRID 1653905Notes

Reaction equation

HRID 1653905 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[OH-].[K+].C1(C=CC(O)=CC=1)O.O>C(O)C.C(O)(=O)C>[CH:3]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=2)(=[O:11])=[O:12])=[CH:8][CH:9]=1)=[CH2:2]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 962WaterHCID 14797Potassium HydroxideHCID 194234114-(2-Bromoethyl)-N-(3-methyl-2-pyridinyl)benzenesulfonamide

Product 1

HCID 194233654-Ethenyl-N-(3-methyl-2-pyridinyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

4-(2-Bromoethyl)-N-(3-methyl-2-pyridinyl)benzenesulfonamide (183 g, 0.5 mol) and potassium hydroxide (120 g, 1.83 mol) and hydroquinone (1 g) in ethanol (2 l) was refluxed for 1 h. 5 l water was added and the solution acidified with acetic acid. The precipitated product was collected by filtration, washed with water and dried. Yield 137 g (quantitative).

Workup

  1. filtrationThe precipitated product was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-29642ee3882e42789dc12141389d09b9
Source dataset
uspto-grants-1995_04
Patent number
US05403930

Reaction notes

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