Diaminomaleonitrile → HCID 68546627, compound

HRID 1591079Notes

Reaction equation

HRID 1591079 reaction equation
[NH2:1]/[C:2](/[C:7]#[N:8])=[C:3](\[NH2:6])/[C:4]#[N:5].[Cl:9][C:10]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([Cl:22])[C:11]=1[CH:12]=O>CO>[NH2:1][C:2]([C:7]#[N:8])=[C:3]([N:6]=[CH:12][C:11]1[C:14]([Cl:22])=[CH:15][C:16]([C:18]([F:19])([F:20])[F:21])=[CH:17][C:10]=1[Cl:9])[C:4]#[N:5]

Participants

4

Reactant 2

HCID 2723951DiaminomaleonitrileHCID 147939142,6-Dichloro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 68546627HCID 68546627, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diaminomaleonitrile (4.4 g, 0.04 mol) was dissolved in methanol (100 ml) and 2,6-dichloro-4-trifluoromethylbenzaldehyde (9.6 g, 0.04 mol) was added with stirring at ambient temperature. The reaction mixture was stirred for 30 minutes and heated at reflux for 1 hour. After cooling to 10° C. a solid which had separated was filtered off to give 1-amino-2-(2,6-dichloro-4-trifluoromethylbenzylideneamino)- 1,2-dicyanoethylene (10.3 g) as a yellow crystalline solid, m.p. 218°-219° C.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. temperatureheated
  3. temperatureat reflux for 1 hour
  4. temperatureAfter cooling to 10° C. a solid which
  5. customhad separated
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-9aeb0475165b4aa1a188cc5be56bc68a
Source dataset
uspto-grants-1993_04
Patent number
US05206257

Reaction notes

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