Ammonia → HCID 13638032, compound

HRID 1579982Notes

Reaction equation

HRID 1579982 reaction equation
BrBr.[C:3]([C:5]([C:22]#[N:23])=[N:6][C:7]([CH3:21])=[C:8]([N:15]1CCOCC1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:4].N>C(Cl)Cl>[C:3]([C:5]1[C:22]([NH2:23])=[N:15][C:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:7]([CH3:21])[N:6]=1)#[N:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 53865096HCID 53865096, compound

Product 1

HCID 13638032HCID 13638032, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reactor provided with a stirring device, a bromine feed and a calcium chloride tube is filled with 1.42 parts of 1,1-dicyano-3-methyl-4-morpholino-4-phenyl-2-aza-1,3-butadiene in 20 parts by volume of dry methylene chloride. 0.34 parts by weight of ammonia in the form of a methanolic solution are added at -30°C. over a period of 4 days. After evaporation of the solvents in vacuo and recrystallisation of the crude product from methanol, 0.95 parts of 2-cyano-3-amino-5-phenyl-6-methyl-pyrazine are obtained in a field of 91% with respect to the starting azadiene.

Workup

  1. customA reactor provided with a stirring device
  2. customAfter evaporation of the solvents
  3. customin vacuo and recrystallisation of the crude product from methanol, 0.95 parts of 2-cyano-3-amino-5-phenyl-6-methyl-pyrazine
  4. customare obtained in a field of 91% with respect to the starting azadiene

Sources & evidence

ORD record
ord-a8883a496e7649708494364a3e7d4201
Source dataset
uspto-grants-1976_01
Patent number
US03932404

Reaction notes

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