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

HRID 2416939Notes

Reaction equation

HRID 2416939 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, 1N 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, 1N 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-83c3394e40fd492092d75e9644bd79cb
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

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