Triethylamine → HCID 22272835, compound

HRID 1064820Notes

Reaction equation

HRID 1064820 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:21][CH2:22][CH2:23][CH2:24][C:25](Br)=[O:26]>C(Cl)(Cl)Cl.O>[Br:21][CH2:22][CH2:23][CH2:24][C:25]([NH:6][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:11]([CH3:13])[CH3:12])=[O:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 32484DiisopropylanilineHCID 135422464-Bromobutanoyl bromide

Product 1

HCID 22272835HCID 22272835, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2,6-diisopropylaniline (1.77 g, 10 mmol) in chloroform (30 ml) was added triethylamine (1.11 g, 11 mmole), then 4-bromobutyryl bromide (1.95 mg, 10.5 mmol) was slowly dropped thereinto with ice cooling and the mixture was made to react for 20 minutes. The reaction solution was diluted with water and extracted with chloroform. The organic layer was washed with 0.5N HCl, water, aqueous solution of sodium bicarbonate and 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 (120 g of silica gel; developing solvent, hexane:acetone=7:1→5:1) and the resulting crude crystals were recrystallized from hexane-acetone to provide 2.06 g (yield 63%) of 4-bromo-N-(2,6-diisopropylphenyl)butyramide as colorless needles.

Workup

  1. customto react for 20 minutes
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with 0.5N HCl, water, aqueous solution of sodium bicarbonate and saturated sodium chloride solution successively
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by a silica gel column chromatography (120 g of silica gel; developing solvent, hexane:acetone=7:1→5:1)
  7. customthe resulting crude crystals were recrystallized from hexane-acetone

Sources & evidence

ORD record
ord-0a4e545abb644d51bb2d5f945484b759
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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