Toluene → 53984-87-5

HRID 1732244Notes

Reaction equation

HRID 1732244 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1(C)[CH:11]=[CH:10][CH:9]=[CH:8][CH:6]1[NH2:7])[CH3:4].[Br:13][CH:14]([CH3:18])[C:15](Br)=[O:16].[C:19]1(C)C=CC=CC=1>>[Br:13][CH:14]([CH3:18])[C:15]([NH:7][C:6]1[C:8]([CH3:19])=[CH:9][CH:10]=[CH:11][C:5]=1[CH2:3][CH3:4])=[O:16]

Participants

5

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 79047Propanoyl bromide, 2-bromo-HCID 20305842HCID 20305842, compound

Product 1

HCID 439233653984-87-5

Procedure

To a two-phase system, containing an aqueous sodium hydroxide solution (20 g sodium hydroxide in 200 ml water) and a mixture of 13.5 g 2-ethyl-2-methylaniline and 75 ml toluene (cooled to 8° C.), was added dropwise with stirring 25 g 2-bromopropionyl bromide. After this addition, stirring was continued for 15 min. and the formed crystals were filtered off. (Addition of petroleum ether to the filtrate precipitates more product, which can be added to the first crop). Total yield 22.8 g (84%). After recrystallization from ether-petroleum ether, it melted at 181°-182° C.

Workup

  1. additionwas added dropwise
  2. additionAfter this addition
  3. filtrationthe formed crystals were filtered off
  4. custom(Addition of petroleum ether to the filtrate precipitates more product, which
  5. additioncan be added to the first crop)
  6. customAfter recrystallization from ether-petroleum ether, it melted at 181°-182° C.

Sources & evidence

ORD record
ord-d0989d1d30f14bc39066ee4fa25aa277
Source dataset
uspto-grants-1980_12
Patent number
US04237068

Reaction notes

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