Chloromethyl Methyl Ether → N-methoxymethyl-N'-t-butyl-N,N'-dibenzoylhydrazine

HRID 849758Notes

Reaction equation

HRID 849758 reaction equation
[C:1]([N:5]([C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][O:24][CH2:25]Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:23][O:24][CH2:25][N:6]([C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 863071,2-Dibenzoyl-1-(tert-butyl)hydrazine

Product 1

HCID 15294609N-methoxymethyl-N'-t-butyl-N,N'-dibenzoylhydrazine

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

N'-t-butyl-N,N'-dibenzoylhydrazine (2 g, 0.007 M) was stirred at room temperature in a two phase system of toluene-50% sodium hydroxide with 100 mg of phase transfer catalyst (tetra-n-butylammonium hydrogen sulfate). Methoxymethyl chloride (1.2 g, 0.015 M) was added dropwise and the mixture was stirred 3 hours. The layers were separated and the toluene layer was washed several times with water (until the water washes were neutral). The toluene solution was dried over anhydrous magnesium sulfate and the toluene removed under vacuum to afford N-methoxymethyl-N'-t-butyl-N,N'-dibenzoylhydrazine as a thick oil.

Workup

  1. customThe layers were separated
  2. washthe toluene layer was washed several times with water (until the water washes
  3. dry with materialThe toluene solution was dried over anhydrous magnesium sulfate
  4. customthe toluene removed under vacuum

Sources & evidence

ORD record
ord-dbe5410d81da4d528d81a41647eb3253
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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