Malononitrile → 2-(2-Ethyl-4-(2,2-dicyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane

HRID 276307Notes

Reaction equation

HRID 276307 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][C:4]=1[N:11]=[C:12]1[S:16][CH2:15][C:14]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[N:13]1[CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH3:2].[C:26](#[N:30])[CH2:27][C:28]#[N:29]>CCO.N1CCCCC1>[CH2:1]([C:3]1[CH:8]=[C:7]([CH:9]=[C:27]([C:26]#[N:30])[C:28]#[N:29])[CH:6]=[CH:5][C:4]=1[N:11]=[C:12]1[S:16][CH2:15][C:14]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[N:13]1[CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[CH3:2]

Participants

5

Reactant 2

HCID 8010MalononitrileHCID 183160482-(2-Ethyl-4-formylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane

Product 1

HCID 183162292-(2-Ethyl-4-(2,2-dicyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonaneYield 28.5%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(2-ethyl-4-formylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane (Method D11a; 0.037 g, 0.104 mmol) in EtOH (10 mL) was added malononitrile (0.007 g, 0.104 mmol) and piperidine (4 drops). The reaction mixture was stirred at room temp. for 2 h, then concentrated under reduced pressure. The residue was purified by preparative TLC (20% EtOAc/hex) to give 2-(2-ethyl-4-(2,2-dicyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane as a yellow solid (0.012 g, 28%): mp 135-136° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by preparative TLC (20% EtOAc/hex)

Sources & evidence

ORD record
ord-2769b1f1397c4dda9629e5d034c637db
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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