1,1-Dimethylhydrazine → HCID 18388843, compound

HRID 2296965Notes

Reaction equation

HRID 2296965 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[CH2:10][N:11]=[C:12]=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][N:18]([CH3:20])[NH2:19].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:17][N:18]([CH3:20])[NH:19][C:12]([NH:11][CH2:10][C:9]1[CH:14]=[CH:15][CH:16]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)=[O:13]

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 8857Ethyl AcetateHCID 18388844HCID 18388844, compound

Product 1

HCID 18388843HCID 18388843, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2.56 g of this crude 3-phenylbenzylisocyanate in 8 ml of toluene was added dropwise 0.78 g (13 mmol) of N,N-dimethylhydrazine with ice-cooling. The mixture was removed from an ice bath and stirred for 1.5 hours. The reaction mixture 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 1.40 g (5.20 mmol) of 1,1-dimethyl-4-(3-phenylbenzyl)semicarbazide.

Workup

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

Sources & evidence

ORD record
ord-ce0f146f75fc4817860924c9d6f3c5da
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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