Thionyl Chloride → HCID 86601186, compound

HRID 498927Notes

Reaction equation

HRID 498927 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]([CH3:27])[C:17]2=[O:28])=[CH:12][C:3]=1[C:4]([O:6][C@@H:7]([CH3:11])[C:8]([OH:10])=O)=[O:5].S(Cl)([Cl:31])=O>>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[N:18]([CH3:27])[C:17]2=[O:28])=[CH:12][C:3]=1[C:4]([O:6][C@@H:7]([CH3:11])[C:8]([Cl:31])=[O:10])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 68458255HCID 68458255, compound

Product 1

HCID 86601186HCID 86601186, compound

Procedure

5.7 g (14 mmol) of (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]-propionic acid from example 3.2 were dissolved in 50 ml of thionyl chloride, and the reaction mixture was heated under reflux for 3.5 hours. The solution was allowed to cool and concentrated, which gave 5.9 g of (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoyloxy]propionyl chloride.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureto cool
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-48355419a8f7424db5fb3502e70167b0
Source dataset
uspto-grants-2010_08
Patent number
US07767624B2

Reaction notes

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