Ethanol → HCID 21252800, compound

HRID 848972Notes

Reaction equation

HRID 848972 reaction equation
C(OC([N:6]1[CH2:11][CH:10]([O:12][CH2:13][CH3:14])[O:9][C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[N:7]1)=O)C.[OH-].[K+].C(O)C>O>[CH2:13]([O:12][CH:10]1[O:9][C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=2)=[N:7][NH:6][CH2:11]1)[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 53703403HCID 53703403, compound

Product 1

HCID 21252800HCID 21252800, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The crude 6-ethoxy-5,6-dihydro-2-[3-(trifluoromethyl)phenyl]-4H-1,3,4-oxadiazine-4-carboxylic acid ethyl ester (17 g) from Step C above, was mixed with 12 g of KOH, 20 g of ethanol, and 40 g of water to create a reaction mixture. The reaction mixture was refluxed for 6 hours and then cooled. 50 ml of water was then added to the reaction mixture, followed by extraction with ethyl acetate (4×100 ml). The ethyl acetate extracts were conbined, dried (MgSO4) and the solvent removed, to give 7 g of crude 6-ethoxy-5,6-dihydro-2-[3-(trifluoromethyl)phenyl]-4H-1,3,4-oxadiazine, which was not purified and was used in Step E below.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. temperaturecooled
  3. extractionfollowed by extraction with ethyl acetate (4×100 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-7847eeef3ca3484da4f61f58a372e803
Source dataset
uspto-grants-2000_01
Patent number
US06011034

Reaction notes

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