Diethyl Sulfate → N-[4-(diethylamino)-2-methylphenyl]acetamide

HRID 436551

Reaction equation

HRID 436551 reaction equation
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([NH:9][CH2:10][CH3:11])=[CH:7][C:6]=1[CH3:14])[C:2]([CH3:4])=[O:3].S(OCC)(O[CH2:19][CH3:20])(=O)=O.[OH-].[Na+]>O>[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([N:9]([CH2:19][CH3:20])[CH2:10][CH3:11])=[CH:7][C:6]=1[CH3:14])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 214528314-Acetamino-3-methyl-N-ethylaniline

Product 1

HCID 222177N-[4-(diethylamino)-2-methylphenyl]acetamideYield 64.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19.1g (0.1 mole) of 4-acetamino-3-methyl-N-ethylaniline obtained in Example 1, Part C, and 100g of water were mixed, and, after 12.5g of diethyl sulfate were added dropwise thereto while stirring, the entire reaction system was stirred overnight at room temperature. Next, the reaction mixture was neutralized with sodium hydroxide and the crystals separated were recrystallized from methanol to obtain 11.5g of white crystals of 4-acetamino-3-methyl-(N,N-diethyl)aniline.

Workup

  1. stirringthe entire reaction system was stirred overnight at room temperature
  2. customthe crystals separated
  3. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-07f5cee7c9e849128dbff41ea39d7b24
Source dataset
uspto-grants-1977_02
Patent number
US04009205

Linked notes

Loading…