Dichloromethane → Halofenozide

HRID 1708426Notes

Reaction equation

HRID 1708426 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(Cl)Cl.[OH-].[Na+]>O>[C:1]([N:5]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:6][C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chloride2×HCID 14798Sodium HydroxideHCID 1275960HCID 1275960, compound

Product 1

HCID 114994HalofenozideYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a 5 L round bottom flask, equipped with a mechanical stirrer, containing the 571 g of wet N'-tert-butyl-N-(4-chlorobenzoyl)hydrazine intermediate and equipped with a 500 mL addition funnel containing 371 g of benzoyl chloride, is charged 1500 mL of methylene chloride, 250 mL of water and lastly 223 g of 50% by weight aqueous sodium hydroxide. The flask contents are stirred and cooled to 5° C. and the benzoyl chloride is added dropwise during a one hour period so that the temperature of the flask contents does not exceed 10° C. After allowing the flask contents to warm to room temperature, stirring is stopped and the organic and aqueous phases are allowed to separate overnight. The upper aqueous phase is removed by suction and is replaced by 500 mL of fresh water, the heterogeneous mixture is stirred, the phases are allowed to separate and the upper aqueous phase again is removed by suction. This washing procedure is repeated two more times and then 500-800 mL of hexane is added to the organic remainder. The contents are briefly stirred and then are poured onto a glass flitted Buchner funnel. The filter cake is washed extensively with a total of 2 L of hexane followed by 10 L of water and then is dried in vacuo at 65° C. for two days to give 758.2 g of N'-tert-butyl-N-(4-chlorobenzoyl)-N'-benzoylhydrazine as a white powder melting at 197°-198° C.

Workup

  1. customTo a 5 L round bottom flask, equipped with a mechanical stirrer
  2. customequipped with a 500 mL addition funnel
  3. customdoes not exceed 10° C
  4. temperatureto warm to room temperature
  5. stirringstirring
  6. customto separate overnight
  7. customThe upper aqueous phase is removed by suction
  8. stirringthe heterogeneous mixture is stirred
  9. customto separate
  10. customthe upper aqueous phase again is removed by suction
  11. addition500-800 mL of hexane is added to the organic remainder
  12. stirringThe contents are briefly stirred
  13. additionare poured onto a glass
  14. washThe filter cake is washed extensively with a total of 2 L of hexane
  15. customis dried in vacuo at 65° C. for two days

Sources & evidence

ORD record
ord-f250cf8f22b0472ca08f1b92394521ec
Source dataset
uspto-grants-1994_10
Patent number
US05358966

Reaction notes

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