Diphenylhydrazone → HCID 69562380, compound

HRID 413691Notes

Reaction equation

HRID 413691 reaction equation
C(O[CH:4]=[C:5]([C:15]#[N:16])[C:6]([O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])C.[C:17]1([NH:23][N:24]=[CH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC>[CH:25](=[N:24][N:23]([CH:4]=[C:5]([C:15]#[N:16])[C:6]([O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 95800DiphenylhydrazoneHCID 854315292-(Trimethylsilyl)ethyl 2-ethoxymethylenecyanoacetate

Product 1

HCID 69562380HCID 69562380, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2-(Trimethylsilyl)ethyl 2-ethoxymethylenecyanoacetate (10.0 g, 41.4 mmol) and benzaldehyde-phenylhydrazone (8.13 g, 41.4 mmol) were combined in 50 mL xylenes under N2 and heated at reflux for 5 h, cooled to room temperature, then treated with hexane (50 mL) and allowed to stir overnight. The precipitate was filtered off, washed with hexane and dried to afford 5.46 g of crude product. Purification by chromatography afforded 2.69 g (16%) of 2-(trimethylsilyl)ethyl 3-(N′-benzylidene-N-phenylhydrazino)-2-cyanoacrylate, as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. filtrationThe precipitate was filtered off
  4. washwashed with hexane
  5. customdried
  6. customto afford 5.46 g of crude product
  7. customPurification by chromatography

Sources & evidence

ORD record
ord-2d967c03d78b4193a4b7ac4bdebb9fa7
Source dataset
uspto-grants-2003_05
Patent number
US06569860B2

Reaction notes

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