Ammonium Sulfate → 2,6-dimethyl-N-methoxyacetyl-N-acetonylaniline

HRID 1156835Notes

Reaction equation

HRID 1156835 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:3]=1[N:4]([C:8](=[O:12])[CH2:9][O:10][CH3:11])[CH2:5][C:6]#[CH:7].S([O-])([O-])(=O)=[O:19].[NH4+].[NH4+]>S([O-])([O-])(=O)=O.[Hg+2].C(O)=O>[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:3]=1[N:4]([CH2:5][C:6]([CH3:7])=[O:19])[C:8](=[O:12])[CH2:9][O:10][CH3:11]

Participants

5

Reactant 2

HCID 6097028Ammonium SulfateHCID 13150482N-(2-Methoxyacetyl)-N-(2-propynyl)-2,6-dimethylbenzenamine

Product 1

HCID 130713232,6-dimethyl-N-methoxyacetyl-N-acetonylanilineYield 77%

Reagents, catalysts & solvents 2

HCID 24544Mercuric sulfateCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

23.1 g (0.1 mol) of 2,6-dimethyl-N-methoxyacetyl-N-propargyl-aniline in 150 ml of 85% strength formic acid were heated to 80° C., and 0.5 g of mercury sulphate was then added to the reaction mixture. The mixture was stirred for a further 6 hours at 80° C. and, after cooling, saturated ammonium sulphate solution was added to the solution and the mixture was extracted with methylene chloride. After naturalizing the methylene chloride phase with sodium bicarbonate solution, the organic phase was dried with sodium sulphate and concentrated. 20.5 g (77% of theory) of 2,6-dimethyl-N-acetonyl-N-methoxyacetyl-aniline of melting point 56°-57° C. were obtained. ##STR179## Process variant (c)

Workup

  1. temperatureafter cooling
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialthe organic phase was dried with sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-557dbd11282d43afbdb61a362052ac09
Source dataset
uspto-grants-1982_06
Patent number
US04337268

Reaction notes

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