Ammonium Chloride → HCID 20399874, compound

HRID 1981160Notes

Reaction equation

HRID 1981160 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[N:6][C:5]([Cl:10])=[C:4]([Cl:11])[N:3]=1.[CH2:12]([Mg]Cl)[CH:13]=[CH2:14].[Cl-].[NH4+]>O1CCCC1.CCOCC>[NH2:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:14][CH:13]=[CH2:12])=[N:6][C:5]([Cl:10])=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 133678713-Amino-5,6-dichloropyrazine-2-carbaldehydeHCID 178418473HCID 178418473, compound

Product 1

HCID 20399874HCID 20399874, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In 4 ml of tetrahydrofuran and 4 ml of ether there was dissolved 288 mg (1.5 mMol) of 2-amino-5,6-dichloro-3-formylpyrazine prepared as in Example 1, Step B, after which the reaction mixture was cooled in a dry-ice/acetone bath, followed by addition of 2-propenyl magnesium chloride (1.5 ml). The reaction mixture was stirred for 15 minutes, an ammonium chloride solution was then added, followed by stirring for 15 minutes at room temperature, after which ether was added. The resulting aqueous layer was extracted twice with ether, and the combined extracts and ether layer were washed well with water, dried, and the solvent evaporated. The remaining material was passed through a silica gel column and eluted with dichloromethane to obtain the product (120 mg).

Workup

  1. temperatureafter which the reaction mixture was cooled in a dry-ice/acetone bath
  2. stirringby stirring for 15 minutes at room temperature
  3. extractionThe resulting aqueous layer was extracted twice with ether
  4. washthe combined extracts and ether layer were washed well with water
  5. customdried
  6. customthe solvent evaporated
  7. washeluted with dichloromethane

Sources & evidence

ORD record
ord-33cf599c76a64c4d8eaca2b8cd99b3de
Source dataset
uspto-grants-1985_04
Patent number
US04512991

Reaction notes

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