Boron trifluoride etherate → 5-(butylthio)-5,6-dihydro-2-[3-(trifluoromethyl)phenyl]-N-[4-(trifluoromethyl)phenyl]-4H-1,3,4-oxadiazine-4-carboxamide

HRID 1530833Notes

Reaction equation

HRID 1530833 reaction equation
C(O[CH:5]1[CH2:10][O:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:7][N:6]1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1)=[O:22])(=O)C.[CH2:34]([SH:38])[CH2:35][CH2:36][CH3:37].B(F)(F)F.CCOCC>ClCCl>[CH2:34]([S:38][CH:5]1[CH2:10][O:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:7][N:6]1[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=1)=[O:22])[CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8012ButanethiolHCID 21252794HCID 21252794, compound

Product 1

HCID 155099635-(butylthio)-5,6-dihydro-2-[3-(trifluoromethyl)phenyl]-N-[4-(trifluoromethyl)phenyl]-4H-1,3,4-oxadiazine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−78° C.) mixture of 3.0 g 5,6-dihydro-5-acetyloxy-2-[3-(trifluoromethyl)phenyl]-N-[4-(trifluoro-methyl)phenyl]-4H-1,3,4-oxadiazine-4-carboxamide (prepared in D above) and 2.0 ml butanethiol in 50 ml dichloromethane was added 1.0 ml borontrifluoride etherate. The cooling bath was removed and the mixture was stirred for 1 h. The mixture was then quenched with saturated sodium bicarbonate and the phases were separated. The organic phase was washed with 1 M sodium hydroxide and saturated sodium bicarbonate, dried over sodium sulfate and concentrated under vacuum to give 5-(butylthio)-5,6-dihydro-2-[3-(trifluoromethyl)phenyl]-N-[4-(trifluoromethyl)phenyl]-4H-1,3,4-oxadiazine-4-carboxamide. The structure was confirmed by 1H NMR.

Workup

  1. temperatureTo a cooled
  2. customThe cooling bath was removed
  3. customThe mixture was then quenched with saturated sodium bicarbonate
  4. customthe phases were separated
  5. washThe organic phase was washed with 1 M sodium hydroxide and saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-11a3badf72884c248867433ab85e38bc
Source dataset
uspto-grants-2001_03
Patent number
US06197766B1

Reaction notes

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