Sodium Hydroxide → Methoxyfenozide

HRID 260809Notes

Reaction equation

HRID 260809 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([NH:8][NH:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:7].[CH3:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[C:22](Cl)=[O:23].[OH-].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([NH:8][N:9]([C:22](=[O:23])[C:21]1[CH:25]=[C:26]([CH3:28])[CH:27]=[C:19]([CH3:18])[CH:20]=1)[C:10]([CH3:13])([CH3:12])[CH3:11])=[O:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 810883,5-Dimethylbenzoyl ChlorideHCID 15376235N'-tert-butyl-3-methoxy-2-methylbenzohydrazide

Product 1

HCID 105010MethoxyfenozideYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine (506 g, 2.14 mole) in methylene chloride (1.5 L) at 5° C. were simultaneously added solutions of 3,5-dimethylbenzoyl chloride (360 g, 2.14 moles) in methylene chloride (500 mL) and sodium hydroxide (50% aqueous, 171.2 g, 2.14 moles) diluted with water (400 mL), at such a rate that the temperature of the mixture did not exceed 10° C. Following the addition, the reaction mixture was allowed to reach room temperature and stirred continuously for 1 additional hour, whereupon the reaction mixture was diluted with methylene chloride (12 L), washed with water, dried over magnesium sulfate, filtered and stripped to give N-(3-methoxy-2-methylbenzoyl)-N'-(3,5-dimethylbenzoyl)-N'-tert-butylhydrazine (663 g), melting at 204°-204.5° C.

Workup

  1. customat 5° C.
  2. customdid not exceed 10° C
  3. additionthe addition
  4. customto reach room temperature
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-319cf65a938e490aa192fddc2173f663
Source dataset
uspto-grants-1996_06
Patent number
US05530028

Reaction notes

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