Phosphorus oxychloride → HCID 54233444, compound

HRID 1982709Notes

Reaction equation

HRID 1982709 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8]C=O)[N:5]=[C:4]([C:11](=[N:17][O:18][CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:3]=1.P(Cl)(Cl)(Cl)=O>C(O)C>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[N:3]=[C:4]([C:11](=[N:17][O:18][CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 54503124HCID 54503124, compound

Product 1

HCID 54233444HCID 54233444, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(4-chloro-6-formamidopyrimidin-2-yl)-2-methoxyiminoacetate (syn isomer) (17 g) in ethanol (255 ml) was added dropwise phosphoryl chloride (14.7 g) under cooling in an ice bath. The mixture was stirred for 1.5 hours at ambient temperature and evaporated to dryness. The residue was dissolved in a mixture of ethyl acetate and water and adjusted to pH 7 with an aqueous solution of sodium bicarbonate. The organic layer was separated out, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was triturated with n-hexane to give ethyl 2-(4-amino-6-chloropyrimidin-2-yl)-2-methoxyiminoacetate (syn isomer) (9.99 g), mp 136°-142° C.

Workup

  1. temperatureunder cooling in an ice bath
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  4. customThe organic layer was separated out
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-9aaf066e8da44d4cbe456d29032cb212
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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