1,1-Dimethylhydrazine → N-(1'-methoxycarbonyl-ethyl)-N-(N',N'-dimethyl-hydrazinoacetyl)-2,6-dimethylaniline

HRID 1706419Notes

Reaction equation

HRID 1706419 reaction equation
[CH3:1][N:2]([CH3:4])[NH2:3].[CH3:5][O:6][C:7]([CH:9]([N:11]([C:20](=[O:23])[CH2:21]Cl)[C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:19])[CH3:10])=[O:8].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]([CH:9]([N:11]([C:20](=[O:23])[CH2:21][NH:3][N:2]([CH3:4])[CH3:1])[C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:19])[CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 14798Sodium HydroxideHCID 6452743DL-Alanine, N-(chloroacetyl)-N-(2,6-dimethylphenyl)-, methyl ester

Product 1

HCID 13132232N-(1'-methoxycarbonyl-ethyl)-N-(N',N'-dimethyl-hydrazinoacetyl)-2,6-dimethylanilineYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

18 g (0.3 mol) of N,N-dimethylhydrazine is added at room temperature to 28.4 g (0.1 mol) of N-(1'-methoxycarbonyl-ethyl)-N-chloroacetyl-2,6-dimethylaniline in 150 ml of toluene. The reaction mixture is then stirred at 50°-60° C. for 96 hours. After cooling to room temperature, there is added about 100 ml of 1 N sodium hydroxide solution, and the organic phase is separated. The aqueous solution is extracted with toluene, the toluene solutions are combined, and washed once with water. After being dried with sodium sulfate, the toluene solution is concentrated in a water-jet vacuum. The brown oil remaining is taken up in petroleum ether, whereupon the product crystallises and is filtered off. The petroleum ether solution is concentrated by evaporation to leave 7.7 g of product in the form of brown oil; nD21 =1.5272.

Workup

  1. customthe organic phase is separated
  2. extractionThe aqueous solution is extracted with toluene
  3. washwashed once with water
  4. dry with materialAfter being dried with sodium sulfate
  5. concentrationthe toluene solution is concentrated in a water-jet vacuum
  6. customcrystallises
  7. filtrationis filtered off
  8. concentrationThe petroleum ether solution is concentrated by evaporation

Sources & evidence

ORD record
ord-08a06cdfc0af469589e7bb59f61d6199
Source dataset
uspto-grants-1980_06
Patent number
US04207338

Reaction notes

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