2,6-Lutidine → HCID 20230064, compound

HRID 638149Notes

Reaction equation

HRID 638149 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].NC1C=[CH:12][C:11]([NH:14][NH:15][CH:16]=[O:17])=[CH:10][CH:9]=1.[N:18]1C(C)=CC=[CH:20][C:19]=1C>C(#N)C>[CH2:19]([NH:18][C:4]([O:3][C:1]1[CH:9]=[CH:10][C:11]([NH:14][NH:15][CH:16]=[O:17])=[CH:12][CH:2]=1)=[O:5])[CH3:20]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 10928Ethyl chloroformateHCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

Product 1

HCID 20230064HCID 20230064, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethylchloroformate (9.01 g., 0.066 mol) was added dropwise to a suspension of 4-amino-1-(2'-formylhydrazino)benzene (10.0 g., 0.066 mol) and 2,6-lutidine (7.1 g, 0.066 mol) in acetonitrile (250 ml). Upon heating to reflux, the reaction mixture became homogeneous. After three hours the reaction had gone to completion as evidenced by thin layer chromatographic examination. The solvent was removed under reduced pressure. The resulting solid was slurried in water and filtered to remove any water soluble amine starting material. The collected solid was slurried in diethyl ether and filtered to remove ether soluble impurities. The collected solid was recrytallized from methanol to yield a white solid (11.4 g., 77% of theoretical yield, melting point 134° C.).

Workup

  1. temperatureUpon heating
  2. temperatureto reflux
  3. customThe solvent was removed under reduced pressure
  4. filtrationfiltered
  5. customto remove any water soluble amine starting material
  6. filtrationfiltered
  7. customto remove ether soluble impurities
  8. customto yield a white solid (11.4 g., 77% of theoretical yield, melting point 134° C.)

Sources & evidence

ORD record
ord-f9656240352b49ee939ce13f4eb57856
Source dataset
uspto-grants-1985_12
Patent number
US04560638

Reaction notes

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