Pyridine → HCID 19832701, compound

HRID 2051100Notes

Reaction equation

HRID 2051100 reaction equation
[CH3:1][O:2][N:3]([CH3:26])[C:4](=[O:25])[C:5]1[CH:10]=[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[NH:13][C:12]2=O)[C:8]([F:23])=[CH:7][C:6]=1[Cl:24].P(Cl)(Cl)([Cl:29])=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][N:3]([CH3:26])[C:4](=[O:25])[C:5]1[CH:10]=[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]=[C:12]2[Cl:29])[C:8]([F:23])=[CH:7][C:6]=1[Cl:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 19832688HCID 19832688, compound

Product 1

HCID 19832701HCID 19832701, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.98 g of N-methoxy-N-methyl-2-chloro-5-[3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzamide, 1.5 ml of phosphorus oxychloride and 1.2 ml of pyridine in 10 ml of toluene is stirred at 80° C. for 3.5 hours. The mixture is then treated with 50 ml of ice-water and extracted three times with 80 ml of ethyl acetate each time. The combined organic phases are washed to neutrality, dried over anhydrous sodium sulphate and treated with 200 ml of n-hexane, and the mixture is filtered through 20 g of silica gel. The mixture is then concentrated and the product is left to crystallize out. In this manner there is obtained N-methoxy-N-methyl-2-chloro-5-[2-chloro-4-oxo-6-trifluoromethyl-3(4H)-pyrimidinyl]-4-fluorobenzamide, m.p. 183° C.;

Workup

  1. extractionextracted three times with 80 ml of ethyl acetate each time
  2. washThe combined organic phases are washed to neutrality
  3. dry with materialdried over anhydrous sodium sulphate
  4. additiontreated with 200 ml of n-hexane
  5. filtrationthe mixture is filtered through 20 g of silica gel
  6. concentrationThe mixture is then concentrated
  7. waitthe product is left
  8. customto crystallize out

Sources & evidence

ORD record
ord-2de048745d8946adb74b03076a183668
Source dataset
uspto-grants-1991_05
Patent number
US05017211

Reaction notes

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