Water → (E)-3-(3,5-Diisopropyl-4-hydroxyphenyl)-2-[(pyrid-2-yl)sulfonyl]acrylonitrile

HRID 1976188Notes

Reaction equation

HRID 1976188 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])[CH:7]=O)([CH3:3])[CH3:2].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([CH2:25][C:26]#[N:27])(=[O:24])=[O:23].O>N1CCCCC1.C(O)C>[CH:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[C:25](/[S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=2)(=[O:24])=[O:23])\[C:26]#[N:27])[CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeHCID 5193552-Pyridinesulfonylacetonitrile

Product 1

HCID 10177190(E)-3-(3,5-Diisopropyl-4-hydroxyphenyl)-2-[(pyrid-2-yl)sulfonyl]acrylonitrileYield 43.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

The reaction mixture of 450.0 mg of 3,5-diisopropyl-4-hydroxylbenzaldehyde, 400.0 mg of 2-pyridinesulphonylacetonitrile and a few drops of piperidine in 10.0 mL of ethanol was refluxed for 3 h and then cooled to room temperature. To the above reaction mixture was added 5.0 mL of water until crystallization began. After standing at 0° C. for 2 h, the solid was filtered, washed with cold water and dried in oven at 40° C. overnight to provide 350.0 mg of the titled compound.

Workup

  1. temperaturewas refluxed for 3 h
  2. customuntil crystallization
  3. filtrationthe solid was filtered
  4. washwashed with cold water
  5. customdried in oven at 40° C. overnight

Sources & evidence

ORD record
ord-0d30ee6007994bae908ce3a7fb03b66a
Source dataset
uspto-grants-2001_05
Patent number
US06225346B1

Reaction notes

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