2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14416606, compound

HRID 1728949Notes

Reaction equation

HRID 1728949 reaction equation
[NH2:1]/[C:2](=[C:5](\[N:8]=[CH:9][O:10][CH3:11])/[C:6]#[N:7])/[C:3]#[N:4].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(#N)C>[CH3:11][O:10][C:9]1[NH:8][C:5]([C:6]#[N:7])=[C:2]([C:3]#[N:4])[N:1]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15721934HCID 15721934, compound

Product 1

HCID 14416606HCID 14416606, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the above 2-amino-3-(methoxymethylenamino) maleonitrile (20 g; 0. 11 mol) and 2,3-dichloro-5,6-dicyanobenzoquinone (25.5 g; 0.11 mol) in acetonitrile (750 mL) was heated at reflux for 4 days. Silica gel (100 g) was added and the acetonitrile was removed in vacuo. The silica gel was extracted with dichloromethane. The dichloromethane solution was concentrated to dryness in vacuo, the yellow residue was suspended in dichloromethane (150 mL) and the mixture was stirred. The mixture was filtered and the filtrate was concentrated in vacuo to yield a light yellow solid that was crystallized from water to give 2-methoxy-4,5-imidazoledicarbonitrile (mp 137°-138° C.).

Workup

  1. temperatureat reflux for 4 days
  2. additionSilica gel (100 g) was added
  3. customthe acetonitrile was removed in vacuo
  4. extractionThe silica gel was extracted with dichloromethane
  5. concentrationThe dichloromethane solution was concentrated to dryness in vacuo
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customto yield a light yellow solid
  9. customthat was crystallized from water

Sources & evidence

ORD record
ord-620fa26816f149a7a165b5d4fae5ac1a
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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