Dichloromethane → HCID 13638030, compound

HRID 1579980Notes

Reaction equation

HRID 1579980 reaction equation
BrBr.[C:3]([C:5]([C:17]([O:19][CH3:20])=[O:18])=[N:6][C:7]([CH3:16])=[C:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:4].C(Cl)Cl.C[O-].[Na+]>CO>[CH3:20][O:19][C:17]([C:5]1[C:3]([NH2:4])=[N:15][C:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:7]([CH3:16])[N:6]=1)=[O:18]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24408BromineHCID 10942334Sodium MethoxideHCID 73186002HCID 73186002, compound

Product 1

HCID 13638030HCID 13638030, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A reactor provided with a stirring device, a bromine feed and a calcium chloride tube is filled with a solution of 4 parts of 1-cyano-1-methoxycarbonyl-3-methyl-4-amino-4-phenyl-2-aza-1,3-butadiene in 120 parts by volume of a mixture of dry methanol and dry methylene chloride (10 : 1 by volume.) 0.9 parts of sodium methylate dissolved in dry methanol are added rapidly at the ambient temperature with stirring. The reaction is finished at the end of 15 minutes, and the greater part of the solvents is evaporated under reduced pressure. The 2-methoxycarbonyl-3-amino-5-phenyl-6-methyl pyrazine which is precipitated is filtered off, then recrystallised from methanol and 3 parts of pyrazine are obtained. M.p. 162°C.

Workup

  1. customA reactor provided with a stirring device
  2. additionare added rapidly at the ambient temperature
  3. customis finished at the end of 15 minutes
  4. customthe greater part of the solvents is evaporated under reduced pressure
  5. customThe 2-methoxycarbonyl-3-amino-5-phenyl-6-methyl pyrazine which is precipitated
  6. filtrationis filtered off
  7. customrecrystallised from methanol and 3 parts of pyrazine
  8. customare obtained

Sources & evidence

ORD record
ord-3cff61d3f9624e8889ca1b290f4d2671
Source dataset
uspto-grants-1976_01
Patent number
US03932404

Reaction notes

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