Ethanol → HCID 20290836, compound

HRID 1413820Notes

Reaction equation

HRID 1413820 reaction equation
[CH3:1][C:2]1[C:11]2[CH:12]=[C:13]([C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][O:8]3)[C:4](=[O:25])[CH:3]=1.[H-].[Na+].S(OC)(O[CH3:32])(=O)=O.C(O)C>CN(C)C=O.O>[CH3:1][C:2]1[C:11]2[CH:12]=[C:13]([C:15]([O:24][CH3:32])([C:16]([F:17])([F:18])[F:19])[C:20]([F:23])([F:22])[F:21])[CH:14]=[C:9]3[C:10]=2[N:5]([CH2:6][CH2:7][O:8]3)[C:4](=[O:25])[CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 20290820HCID 20290820, compound

Product 1

HCID 20290836HCID 20290836, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

to a solution of 2,3-dihydro-7-methyl-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-5H-pyrido[1,2,3-de]-1,4-benzoxazin-5-one in dimethylformamide is added sodium hydride and dimethyl sulfate. The solution is stirred for 24 hours, treated with ethanol and added to water. The resultant recipitate is filtered, triterated with 10% sodium hydroxide solution and filtered. The residual solid is recrystallized to give 2,3-dihydro-7-methyl-9-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl) ethyl]-5H-pyrido[1,2,3-de]-1,4-benzoxazin-5-one. If desired sodium hydride may be replaced by a base such as potassium carbonate or potassium t-butoxide and dimethyl sulfate may be replaced by methyl iodide.

Workup

  1. filtrationThe resultant recipitate is filtered
  2. filtrationfiltered
  3. customThe residual solid is recrystallized

Sources & evidence

ORD record
ord-ea0af21fdece4c85b63eab0d966ad75f
Source dataset
uspto-grants-1981_02
Patent number
US04251534

Reaction notes

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