Diazomethane → HCID 54343679, compound

HRID 2286663Notes

Reaction equation

HRID 2286663 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10](=[N:16][OH:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:5]=1)=[O:2].[N+](=[CH2:20])=[N-]>O1CCOCC1.C(OCC)C>[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10](=[N:16][O:17][CH3:20])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:5]=1)=[O:2]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 136335647HCID 136335647, compound

Product 1

HCID 54343679HCID 54343679, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-(4-formamidopyrimidin-2-yl)-2-hydroxyiminoacetate (7.0 g.) was dissolved in dioxane (200 ml.) under heating and the resultant solution was cooled to ambient temperature in an ice bath, and then thereto was added a solution of diazomethane in diethyl ether with stirring until complete consumption of the starting materials. The reaction mixture was concentrated to give a brown oil, which was purified by column chromatography on silica gel (140 g.) using benzene as an developing solvent and a mixture of benzene and ethyl acetate (3:1) as an eluent to give a pale brown semisolid of ethyl 2-(4-formamidopyrimidin-2-yl)-2-methoxyiminoacetate (4.4 g.).

Workup

  1. temperatureunder heating
  2. concentrationThe reaction mixture was concentrated
  3. customto give a brown oil, which
  4. customwas purified by column chromatography on silica gel (140 g.)
  5. additiona mixture of benzene and ethyl acetate (3:1) as an eluent

Sources & evidence

ORD record
ord-ee5597992298445997bc49178424b999
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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