Bromoacetic Acid → Acetamide, N-[2,6-bis(1-methylethyl)phenyl]-2-bromo-

HRID 1532698Notes

Reaction equation

HRID 1532698 reaction equation
Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH:23]([C:26]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]([CH3:35])[CH3:34])[C:27]=1[NH2:28])([CH3:25])[CH3:24].[Br:36][CH2:37][C:38](O)=[O:39]>CN(C)C=O>[Br:36][CH2:37][C:38]([NH:28][C:27]1[C:26]([CH:23]([CH3:25])[CH3:24])=[CH:32][CH:31]=[CH:30][C:29]=1[CH:33]([CH3:35])[CH3:34])=[O:39]

Participants

6

Reactant 4

HCID 6227Bromoacetic AcidHCID 32484DiisopropylanilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 12149064Acetamide, N-[2,6-bis(1-methylethyl)phenyl]-2-bromo-Yield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3′-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC) (2.1 g, 11 mmols) and 1-hydroxybenzotriazole (HOBt) (1.49 g, 11 mmols) were added to an N,N-dimethylformamide (DMF) (30 ml) solution of 2,6-diisopropylaniline (1.97 g, 10 mmols) and bromoacetic acid (2.08 g, 15 mmols), and stirred at room temperature for 12 hours. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, 1 N HCl, an aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate, and the solvent was evaporated. Then, the residue was purified through silica gel column chromatography (developer: hexane/acetone=5/1), and the resulting crystals were recrystallized from ether-hexane to obtain 1.26 g (42%) of 2-bromo-N-(2,6-diisopropylphenyl)acetamide as colorless needle-like crystals.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, 1 N HCl
  3. dry with materialan aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThen, the residue was purified through silica gel column chromatography (developer: hexane/acetone=5/1)
  6. customthe resulting crystals were recrystallized from ether-hexane

Sources & evidence

ORD record
ord-7cdf7126ec4446ad8bd40b9ac7d7a93b
Source dataset
uspto-grants-2001_03
Patent number
US06204278B1

Reaction notes

Loading…