Dimethylformamide → 6-Chloro-5-formyl-1,3-dimethyluracil

HRID 1891091Notes

Reaction equation

HRID 1891091 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][N:7]1[C:14](=[O:15])[CH2:13][C:11](=O)[N:10]([CH3:16])[C:8]1=[O:9].CN(C)[CH:19]=[O:20]>>[Cl:3][C:11]1[N:10]([CH3:16])[C:8](=[O:9])[N:7]([CH3:6])[C:14](=[O:15])[C:13]=1[CH:19]=[O:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 69860Dimethylbarbituric acid

Product 1

HCID 3199716-Chloro-5-formyl-1,3-dimethyluracil

Procedure

Phosphorous oxychloride (690 ml) was added slowly to dry N,N-dimethyl formamide (180 ml) at 0° C. The mixture was then allowed to warm to room temperature. 1,3-Dimethylbarbituric acid (60 g, 384.27 mmol) was added portion wise and refluxed for 45 min. The excess of phosphorous oxychloride and DMF were distilled off under reduced pressure and the viscous residue was poured into ice-cold water (2000 ml). The reaction mixture was allowed to room temperature and extracted with chloroform (3×500 ml).

Workup

  1. temperaturerefluxed for 45 min
  2. distillationThe excess of phosphorous oxychloride and DMF were distilled off under reduced pressure
  3. additionthe viscous residue was poured into ice-cold water (2000 ml)
  4. customwas allowed to room temperature
  5. extractionextracted with chloroform (3×500 ml)

Sources & evidence

ORD record
ord-bdfa166216984279b50c960c710194eb
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

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