Phosphorus oxychloride → HCID 16660078, compound

HRID 2356350Notes

Reaction equation

HRID 2356350 reaction equation
O[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:9])=[C:6]([S:18][CH3:19])[N:5]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:35])=O>>[Cl:35][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:9])=[C:6]([S:18][CH3:19])[N:5]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178503123HCID 178503123, compound

Product 1

HCID 16660078HCID 16660078, compoundYield 57%

Procedure

4-Hydroxy-N-(4-methylphenyl)-6-(methylthio)-2-[4-(methylthio)phenyl] pyrimidine-5-carboxamide (0.5 g, 1.25 mmol) was refluxed in phosphorus oxychloride (10 ml) for 3 hours and subsequently cooled to room temperature. The reaction mixture was poured onto ice-water mixture, neutralised with saturated sodium bicarbonate solution and the solid thus separated was extracted with ethylacetate. The organic layer was washed with water; dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound, 0.3 g, yield 57%.

Workup

  1. additionThe reaction mixture was poured onto ice-water mixture
  2. customthe solid thus separated
  3. extractionwas extracted with ethylacetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8c729971b9648398b8dc202d5da5e9a
Source dataset
uspto-grants-2010_07
Patent number
US07759350B2

Reaction notes

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