Malononitrile → HCID 53672594, compound

HRID 362296Notes

Reaction equation

HRID 362296 reaction equation
CC(C)([O-])C.[K+].[C:7](#[N:11])[CH2:8][C:9]#[N:10].[C:12]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25](=O)[CH2:26][Cl:27])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[Cl:27][C:26]1[CH:25]=[CH:20][CH:21]=[CH:22][C:23]=1[C:24]1[C:8]([C:9]#[N:10])=[C:7]([NH2:11])[N:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 23665647Potassium tert-butoxideHCID 54065816HCID 54065816, compound

Product 1

HCID 53672594HCID 53672594, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

4.0 g of potassium tertiary butoxide are dissolved in 80 ml of ethanol and subsequently first 3.0 g of malononitrile and then 9 g of 2'-phenylamino-2-chloroacetophenone are added at RT and the mixture is stirred at 65° C. for 2 h. The mixture is then cooled and concentrated in an RE. The residue is partitioned between water and methylene chloride and the aqueous phase is extracted once more with methylene chloride. The combined organic phases are dried over MgSO4 and concentrated. The product is chromatographed on silica gel using methylene chloride and the product-containing fractions are concentrated, 4-(2-chlorophenyl)-1-phenyl-2-amino-3-cyanopyrrole being obtained as a reddish, viscous oil which is directly further processed.

Workup

  1. temperatureThe mixture is then cooled
  2. concentrationconcentrated in an RE
  3. customThe residue is partitioned between water and methylene chloride
  4. extractionthe aqueous phase is extracted once more with methylene chloride
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. concentrationconcentrated
  7. customThe product is chromatographed on silica gel
  8. concentrationthe product-containing fractions are concentrated

Sources & evidence

ORD record
ord-f7f5f820dcd94c93b7d0659171a33966
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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