Phosphorus oxychloride → HCID 13556945, compound

HRID 1165777Notes

Reaction equation

HRID 1165777 reaction equation
[Cl:1][C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[N:5]([CH2:11][CH3:12])[C:4](=[O:13])[C:3]=1[CH:14]=[N:15]O.P(Cl)(Cl)(Cl)=O>O1CCCC1>[Cl:1][C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[N:5]([CH2:11][CH3:12])[C:4](=[O:13])[C:3]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86743819HCID 86743819, compound

Product 1

HCID 13556945HCID 13556945, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the oxime (16 g) in tetrahydrofuran (320 ml)was added dropwise phosphorus oxychloride (30 g) with stirring. The reaction mixture was concentrated under reduced pressure. To the concentrate was added diisopropylether(200 ml), whereupon 6-chloro-5-cyano-1,3-diethylpyrimidine-2,4(1H,3H)-dione precipitated out as pale yellow prisms(12.4 g), m.p. 92°-94° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the concentrate was added diisopropylether(200 ml)
  3. customwhereupon 6-chloro-5-cyano-1,3-diethylpyrimidine-2,4(1H,3H)-dione precipitated out as pale yellow prisms(12.4 g), m.p. 92°-94° C.

Sources & evidence

ORD record
ord-7c882f75ca0b401bbc5523db4c3f40c9
Source dataset
uspto-grants-1990_03
Patent number
US04912104

Reaction notes

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