Triethylamine → HCID 22247152, compound

HRID 1064803Notes

Reaction equation

HRID 1064803 reaction equation
C(N(CC)CC)C.[CH:8]([C:11]1[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:15]=[C:14]([CH:21]([CH3:23])[CH3:22])[C:12]=1[NH2:13])([CH3:10])[CH3:9].[Br:24][CH2:25][C:26](Br)=[O:27]>C(Cl)(Cl)Cl>[Br:24][CH2:25][C:26]([NH:13][C:12]1[C:11]([CH:8]([CH3:10])[CH3:9])=[CH:17][C:16]([CH:18]([CH3:20])[CH3:19])=[CH:15][C:14]=1[CH:21]([CH3:23])[CH3:22])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 5198712,4,6-Tris(1-methylethyl)benzenamine

Product 1

HCID 22247152HCID 22247152, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (111 mg, 1.1 mmol) was added to a solution of 2,4,6-triisopropylaniline (219 mg, 1.0 mmol) in chloroform (3 ml), then bromoacetyl bromide (222 mg, 1.1 mmol) was gradually dropped thereinto with ice-cooling and the mixture was stirred for 1 hour. The reaction mixture was concentrated and the residue was extracted with ethyl acetate. The organic layer was washed with diluted hydrochloric acid, an aqueous solution of sodium bicarbonate and a saturated sodium chloride solution successively and dried over magnesium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (15 g of silica gel; developing solvent, hexane:acetone=5:1) followed by recrystallizing from hexane-ether to provide 275 mg (yield 81%) of 2-Bromo-N-(2,4,6-triisopropylphenyl)acetamide as colorless needles.

Workup

  1. temperaturewith ice-cooling
  2. concentrationThe reaction mixture was concentrated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with diluted hydrochloric acid
  5. dry with materialan aqueous solution of sodium bicarbonate and a saturated sodium chloride solution successively and dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by a silica gel column chromatography (15 g of silica gel; developing solvent, hexane:acetone=5:1)
  8. customby recrystallizing from hexane-ether

Sources & evidence

ORD record
ord-58a1726810684081bda975131c9d9c53
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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