Triethylamine → 2,6-dimethyl-N-(2-methoxyimino-prop-1-yl)-N-methoxyacetylaniline

HRID 1156836Notes

Reaction equation

HRID 1156836 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:3]=1[N:4]([C:9](=[O:13])[CH2:10][O:11][CH3:12])[CH2:5][C:6]([CH3:8])=O.Cl.[CH3:20][O:21][NH2:22].C(N(CC)CC)C>C(O)C>[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:3]=1[N:4]([CH2:5][C:6](=[N:22][O:21][CH3:20])[CH3:8])[C:9](=[O:13])[CH2:10][O:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 130713232,6-dimethyl-N-methoxyacetyl-N-acetonylaniline

Product 1

HCID 541605692,6-dimethyl-N-(2-methoxyimino-prop-1-yl)-N-methoxyacetylanilineYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 g (0.08 mol) of 2,6-dimethyl-N-methoxyacetyl-N-acetonylaniline, 7.5 g (0.09 mol) of O-methyl-hydroxylamine hydrochloride and 9.1 g (0.09 mol) of triethylamine in 100 ml of ethanol were heated under reflux for 5 hours. After distilling off the solvent in vacuo, the residue was partitioned between water/methylene chloride. The organic phase was separated off, dried over sodium sulphate and concentrated. After adding petroleum ether, the residue crystallized. 21 g (94% of theory) of 2,6-dimethyl-N-(2-methoxyimino-prop-1-yl)-N-methoxyacetylaniline of melting point 56°-57° C. were obtained.

Workup

  1. temperatureunder reflux for 5 hours
  2. distillationAfter distilling off the solvent in vacuo
  3. customthe residue was partitioned between water/methylene chloride
  4. customThe organic phase was separated off
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. additionAfter adding petroleum ether
  8. customthe residue crystallized

Sources & evidence

ORD record
ord-e0d31e4f7f3d40dd8c90e5b93ad8b457
Source dataset
uspto-grants-1982_06
Patent number
US04337268

Reaction notes

Loading…