Malononitrile → HCID 53917549, compound

HRID 362302Notes

Reaction equation

HRID 362302 reaction equation
[Na].[C:2](#[N:6])[CH2:3][C:4]#[N:5].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28](=O)[CH3:29])[CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C>[C:26]1([C:27]2[C:3]([C:4]#[N:5])=[C:2]([NH2:6])[N:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH2:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:16]=3)[CH:22]=2)[CH:25]=[CH:24][CH:23]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 5360545SodiumHCID 53911750HCID 53911750, compound

Product 1

HCID 53917549HCID 53917549, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

0.95 g of sodium is dissolved in 200 ml of ethanol and subsequently first 2.98 g of malononitrile and then 11.96 g of 2'-(3-benzyloxyphenylamino)acetophenone are added at RT and the mixture is stirred at 50° 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 twice with methylene chloride. The combined organic phases are dried over Na2SO4 and concentrated, 4-phenyl-1-(3-benzyloxyphenyl)-2-amino-3-cyanopyrrole being obtained. The oily product is employed in the next stage without further purification.

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 twice with methylene chloride
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dd102a20c0c74890b992cb0fc6815b39
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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