3,5-Di-tert-butyl-4-hydroxybenzaldehyde → (E)-2-(Benzylaminosulfonyl)-3-(3,5-di-t-butyl-4-hydroxyphenyl)acrylonitrile

HRID 1976194Notes

Reaction equation

HRID 1976194 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([NH:25][S:26]([CH2:29][C:30]#[N:31])(=[O:28])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C.N1CCCCC1.O>[CH2:18]([NH:25][S:26](/[C:29](=[CH:8]/[C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]([OH:13])=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=1)/[C:30]#[N:31])(=[O:28])=[O:27])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 2

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 15410493HCID 15410493, compound

Product 1

HCID 15410490(E)-2-(Benzylaminosulfonyl)-3-(3,5-di-t-butyl-4-hydroxyphenyl)acrylonitrile

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 250 mg of 3,5-di-t-butyl-4-hydroxybenzaldehyde and 230 mg of N-benzyl cyanomethyl sulfonamide in 2 ml of ethanol with 2 drops of piperidine was heated at 100° C. for 3 hours. The cooled mixture was then diluted with 10 ml of water and extracted with 50 ml of ethyl acetate. The organic extract was then washed with brine, dried over sodium sulfate, filtered and concentrated. Crystallization of the crude with ethyl acetate and hexane yield 206 mg of the titled compound.

Workup

  1. extractionextracted with 50 ml of ethyl acetate
  2. extractionThe organic extract
  3. washwas then washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCrystallization of the crude with ethyl acetate and hexane yield 206 mg of the titled compound

Sources & evidence

ORD record
ord-c195bd31c06546ddb278103d42d5d63f
Source dataset
uspto-grants-2001_05
Patent number
US06225346B1

Reaction notes

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