Triethylamine → HCID 14150245, compound

HRID 464948Notes

Reaction equation

HRID 464948 reaction equation
[CH:1]([NH:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.[N+:19]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26])([O-:21])=[O:20]>C(#N)C>[CH:1]([NH:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

Product 1

HCID 14150245HCID 14150245, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

68.2 g of 1-formyl-2-(4-aminophenyl)hydrazine and 60 ml of triethylamine were dissolved in 500 ml of acetonitrile. To the resulting solution, 70 g of 3-nitrobenzoyl chloride was added dropwise with stirring while keeping the solution temperature at less than 50° C., by which crystals precipitated. After being heated to 60° C. for a further 2 hours, it was cooled and poured into water. Crystals were filtered off and recrystallized from ethanol to obtain 72.8 g of 1-formyl-2-(4-(3-nitrobenzamido)phenyl)hydrazine. Yield: 54%. Melting point: 185°-187° C.

Workup

  1. customat less than 50° C.
  2. customby which crystals precipitated
  3. temperatureit was cooled
  4. additionpoured into water
  5. filtrationCrystals were filtered off
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-51a3d21d64e74489a470540616b5c17d
Source dataset
uspto-grants-1985_10
Patent number
US04550070

Reaction notes

Loading…