Benzene → HCID 70147664, compound

HRID 2305268Notes

Reaction equation

HRID 2305268 reaction equation
[NH2:1]/[C:2](/[C:7]#[N:8])=[C:3](\[NH2:6])/[C:4]#[N:5].[C:9]([CH2:12][C:13](=O)[CH3:14])(=[O:11])C.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:4]([C:3]1[CH:2]([C:7]#[N:8])[NH:1][C:9]([OH:11])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[C:13]([CH3:14])[N:6]=1)#[N:5]

Participants

4

Reactant 3

HCID 241BenzeneHCID 31261AcetylacetoneHCID 2723951Diaminomaleonitrile

Product 1

HCID 70147664HCID 70147664, compound

Procedure

In the presence of a catalytic amount of acetic acid, 2,3-dicyano-5-hydroxy-5-phenyl-7-methyl-4H-1,4-diazepine (compound 5a) was obtained by reacting 1 mol of diaminomaleonitrile with 1 mol of acetylacetone in a solvent (benzene) at 45° C. for 6 hours. The diazepine compound (5a) thus obtained was dehydrated in the presence of phosphorus pentoxide. The object compound 2,3-dicyano-5-phenyl-7-(2-(4-methoxyphenyl)vinyl-1-yl)-6H-1,4-diazepine (compound 5) was obtained by reacting the diazepine compound (5b) thus obtained with 4-methoxybenzaldehyde in the presence of piperidine.

Workup

  1. customat 45° C.
  2. customfor 6 hours

Sources & evidence

ORD record
ord-16d8a8a502b94d798e92d149fcc911b4
Source dataset
uspto-grants-2002_08
Patent number
US06440588B1

Reaction notes

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