Orotic Acid → 2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl chloride

HRID 883536Notes

Reaction equation

HRID 883536 reaction equation
S(Cl)([Cl:3])=O.[C:5]([OH:15])(=O)[C:6]1[NH:13][C:11](=[O:12])[NH:10][C:8](=[O:9])[CH:7]=1>O>[O:12]=[C:11]1[NH:13][C:6]([C:5]([Cl:3])=[O:15])=[CH:7][C:8](=[O:9])[NH:10]1

Participants

4

Reactant 2

HCID 967Orotic AcidHCID 24386Thionyl Chloride3×

Product 1

HCID 204910432,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 13.13 ml (180 mmol) of thionyl chloride, and a water condenser, is placed 15.61 g (100 mmol) of orotic acid. Addition of the thionyl chloride is completed with heating to about 55° C. over the course of about 45 minutes. When addition of the thionyl chloride is complete the mixture is heated and stirred for an additional 45 minutes. The water condenser is then replaced with a distillation side arm condenser and the crude mixture is distilled. The crude distillate in the receiving flask is then fractionally distilled to obtain the acyl chloride, 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl chloride (orotoyl chloride). This acyl chloride, 6.11 g (35 mmol), is put into a dry separatory funnel and combined with 50 mL of dry DCM for use in the next step of the reaction.

Workup

  1. customIn a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer
  2. customfixed with a separatory funnel
  3. temperatureis heated
  4. distillationthe crude mixture is distilled
  5. distillationThe crude distillate in the receiving flask is then fractionally distilled

Sources & evidence

ORD record
ord-2dddd6249ecf42c0abd49d809416facb
Source dataset
uspto-grants-2012_08
Patent number
US08236952B2

Reaction notes

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