Triethylamine → HCID 73682687, compound

HRID 1156837Notes

Reaction equation

HRID 1156837 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[N:4]([CH2:12][C:13]([CH3:15])=O)[C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=[O:6].[Cl-].[OH:22][NH3+:23].C(N(CC)CC)C>C(O)C.C(Cl)Cl>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[N:4]([C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=[O:6])[CH2:12][C:13](=[N:23][OH:22])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 13071322HCID 13071322, compound

Product 1

HCID 73682687HCID 73682687, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

27.1 g (0.1 mol) of 2,6-dimethyl-N-acetonyl-N-(2-furoyl)-aniline, 14 g (0.2 mol) of hydroxyammonium chloride and 15 ml of triethylamine in 150 ml of ethanol were heated under reflux for 3 hours. The reaction mixture was then largely freed from solvent in vacuo, the residue was taken up in methylene chloride and the methylene chloride mixture was washed with water, dried over sodium sulphate and concentrated. The crystalline residue was triturated with ether and the solid was filtered off. 24.4 g (85% of theory) of 2,6-dimethyl-N-(2-furoyl)-N-(2-hydroxyimino-prop-1-yl)-aniline of melting point 155°-156° C. were obtained.

Workup

  1. temperatureunder reflux for 3 hours
  2. washthe methylene chloride mixture was washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crystalline residue was triturated with ether
  6. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-98c6a14363b942c29ed58559d546b273
Source dataset
uspto-grants-1982_06
Patent number
US04337268

Reaction notes

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