Methylamine → 2-Methylamino-4'-butoxy-2',6'-dimethyl-propionanilide

HRID 437141Notes

Reaction equation

HRID 437141 reaction equation
[CH3:1][NH2:2].Br[CH:4]([CH3:21])[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][C:9]=1[CH3:20])=[O:6]>C1C=CC=CC=1>[CH3:1][NH:2][CH:4]([CH3:21])[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][C:9]=1[CH3:20])=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 125468282-Bromo-N-(4-butoxy-2,6-dimethylphenyl)propanamide

Product 1

HCID 214305302-Methylamino-4'-butoxy-2',6'-dimethyl-propionanilide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a cold stirred solution of 14.8 g. of monomethyl amine in 250 ml dry benzene was added (portionwise, keeping temperature below 10°) 19.5 g (0.0594 mole) of 2-bromo-4'-butoxy-2', 6'-dimethyl propionanilide (made according to the procedure in the first part of this example); this dissolved readily forming a clear solution. The mixture was heated to 70° for ca 1 hr. with stirring, at which point a white precipitate had separated and reflux became so vigorous that the reaction had to be controlled by external cooling.

Workup

  1. customtemperature below 10°
  2. dissolutionthis dissolved readily
  3. customforming a clear solution
  4. temperatureThe mixture was heated to 70° for ca 1 hr
  5. customhad separated
  6. temperaturereflux

Sources & evidence

ORD record
ord-ba2dee46afd44af39ffc82014872cc1e
Source dataset
uspto-grants-1977_06
Patent number
US04029793

Reaction notes

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