1,1-Dimethylhydrazine → HCID 73433314, compound

HRID 2296971Notes

Reaction equation

HRID 2296971 reaction equation
[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[CH2:15][N:16]=[C:17]=[O:18])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][N:23]([CH3:25])[NH2:24].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:22][N:23]([CH3:25])[NH:24][C:17]([NH:16][CH2:15][C:14]1[CH:19]=[CH:20][CH:21]=[C:12]([C:10](=[N:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:11])[CH:13]=1)=[O:18]

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 8857Ethyl AcetateHCID 73433325HCID 73433325, compound

Product 1

HCID 73433314HCID 73433314, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 2.75 g of crude 3-(1-(benzyloxyimino)ethyl)benzylisocyanate in 13 ml of dry toluene was added dropwise a solution of 0.53 g (8.74 mmol) of N,N-dimethylhydrazine in 5 ml of dry toluene with ice-cooling. The mixture was removed from an ice bath and stirred for 1 hour. The reaction solution was concentrated, and the residue was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=1:1 and then 1:2) to obtain 0.55 g (1.62 mmol) of 1,1-dimethyl-4-{3-(1-(benzyloxyimino)ethyl)benzyl}-semicarbazide.

Workup

  1. temperaturecooling
  2. customThe mixture was removed from an ice bath
  3. concentrationThe reaction solution was concentrated
  4. washeluted with n-hexane

Sources & evidence

ORD record
ord-afc6990c45af4e90b182d75f7d278e0b
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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