Toluene → 2-Bromo-N-(2-phenylpropan-2-yl)propanamide

HRID 1283945Notes

Reaction equation

HRID 1283945 reaction equation
[CH3:1][C:2]([NH2:10])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-:11].[Na+].BrC[CH2:15][C:16]([Br:18])=O.[C:19]1(C)C=CC=CC=1>>[Br:18][CH:16]([CH3:15])[C:19]([NH:10][C:2]([CH3:9])([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:11]

Participants

5

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 68509CumylamineHCID 10998423Bromopropionylbromide

Product 1

HCID 215169672-Bromo-N-(2-phenylpropan-2-yl)propanamide

Conditions

Temperature
0 °C

Procedure

α,α-dimethylbenzylamine (27.0 g; 0.200 mole) was dissolved in toluene (200 ml), 10 % NaOH (200 ml) was added and the stirred mixture was cooled to 0°C. Bromopropionyl bromide (76.0 g; 0.352 mole) was added dropwise during 30 minutes while keeping the temperature below 10°C. Stirring was continued at room temperature for about 3 hours. The precipitated crystalline 2-bromo-N-(α,α-dimethylbenzyl)propionamide was filtered off, washed on the filter with cold toluene and dried in vacuo at 60°C. Yield: 45.2 g (83.8 %); m.p. 102°-103°C.

Workup

  1. customthe temperature below 10°C
  2. filtrationThe precipitated crystalline 2-bromo-N-(α,α-dimethylbenzyl)propionamide was filtered off
  3. washwashed on the
  4. filtrationfilter with cold toluene
  5. customdried in vacuo at 60°C

Sources & evidence

ORD record
ord-fedcaa352e79475380e458e9c5821fa1
Source dataset
uspto-grants-1976_08
Patent number
US03976771

Reaction notes

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