Sodium Methoxide → HCID 19745780, compound

HRID 2253582Notes

Reaction equation

HRID 2253582 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:6]([C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][C:22](=[O:25])[N:21]([CH2:26][C:27]#[CH:28])[C:20]=3[CH:29]=2)[C:7](=[O:15])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1>CO>[CH3:1][O:2][C:5]1[N:6]([C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][C:22](=[O:25])[N:21]([CH2:26][C:27]#[CH:28])[C:20]=3[CH:29]=2)[C:7](=[O:15])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19745816HCID 19745816, compound

Product 1

HCID 19745780HCID 19745780, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1.08 g of sodium methylate in 10 ml of methanol is added at 20° C. while stirring to a solution of 7.65 g of 6-[2-chloro-6-oxo-4-trifluoromethyl-1(6H)pyrimidinyl]-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one in 300 ml of absolute methanol. A suspension forms during 15 minutes and the temperature rises to 30° C. The reaction mixture is concentrated at 40°-50° C. under reduced pressure and the residue is dissolved in 500 ml of ethyl acetate. The organic phase is washed twice with 200 ml of water each time, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The crystalline residue is stirred with 20 ml of diethyl ether, cooled to 0° C. and treated with 100 ml of n-hexane. The crystals are filtered off under suction and dried at 50° C. under reduced pressure. In this manner there is obtained 6-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one, m.p. 218°-220° C.

Workup

  1. customrises to 30° C
  2. concentrationThe reaction mixture is concentrated at 40°-50° C. under reduced pressure
  3. dissolutionthe residue is dissolved in 500 ml of ethyl acetate
  4. washThe organic phase is washed twice with 200 ml of water each time
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. additiontreated with 100 ml of n-hexane
  8. filtrationThe crystals are filtered off under suction
  9. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-fefbf9af46244de0844c7b6791ea586e
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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