Chlorodifluoromethane → HCID 21274224, compound

HRID 1382140Notes

Reaction equation

HRID 1382140 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][C:10]([CH3:14])=[N:9]2)=[CH:4][C:3]=1[O:15][CH3:16].[OH-].[Na+].[F:19][CH:20]([F:22])Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1CCCCC1>[F:19][CH:20]([F:22])[N:11]1[C:12](=[O:13])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([O:15][CH3:16])[CH:4]=2)[N:9]=[C:10]1[CH3:14]

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 135688048HCID 135688048, compound

Product 1

HCID 21274224HCID 21274224, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 60.0 g (0.28 mole) of 4,5-dihydro-1-(4-methyl-3-methoxyphenyl)-3-methyl-1,2,4-triazol-5(1H)-one, 60.0 g (0.19 mole) of tetrabutylammonium bromide and 60.0 g (1.5 mole) of powdered sodium hydroxide in 2 liters of cyclohexane was heated at reflux. During a two hour period 60.0 g (0.67 mole) of gaseous difluorochloromethane was bubbled into the mixture. After complete addition the mixture was stirred at reflux for one hour, then allowed to cool to 70° C. The supernatant liquid was decanted and washed with aqueous 10% hydrochloric acid followed by an aqueous 10% sodium hydroxide solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave a solid. This solid was triturated with petroleum ether and filtered. The filter cake was air dried to yield 18.5 g of 4-difluoromethyl-4,5-dihydro-1-(4-methyl-3-methoxyphenyl)-3-methyl-1,2,4-triazol-5-(1H)-one.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. additionAfter complete addition the mixture
  4. temperatureat reflux for one hour
  5. customThe supernatant liquid was decanted
  6. washwashed with aqueous 10% hydrochloric acid
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under reduced pressure
  10. customto leave a solid
  11. customThis solid was triturated with petroleum ether
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-6d8df8ce05164be48962ca811fadea42
Source dataset
uspto-grants-1989_02
Patent number
US04806145

Reaction notes

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