Triethylamine → HCID 22633577, compound

HRID 1532716Notes

Reaction equation

HRID 1532716 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[F:10][C:11]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[C:12]=1[NH2:13].C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:13][C:12]1[C:11]([F:10])=[CH:17][C:16]([F:18])=[CH:15][C:14]=1[F:19])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 677652,4,6-TrifluoroanilineHCID 898486-Bromohexanoyl chloride

Product 1

HCID 22633577HCID 22633577, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-Bromohexanoyl chloride (234 mg, 1.1 mmols) was gradualy added dropwise to a chloroform (3 ml) solution of 2,4,6-trifluoroaniline (147 mg, 1.0 mmol) and triethylamine (11 mg, 1.1 mmols) cooling in ice bath, and stirred for 1 hour at room temperature. The reaction mixture was concentrated, and extracted with ethyl acetate. The organic layer was washed with 1N-HCl, an aqueous saturated solution of sodium hydrogencarbonate, water, and saturated saline in that order, and dried with anhydrous sodium sulfate, and the solvent was evaporated. Then, the resulting solid was recrystallized from hexan-ether, and 6-bromo-N-(2,4,6-trifluorophenyl)hexan amide 283 mg(yield 87%) was obtained as colorless needle-like crystals. Potassium carbonate (45 mg, 0.33 mmols) and 18-crown-6 (8 mg, 0.03 mmols) were added to DMF (2 ml) solution of the resulting anilide (97 mg, 0.3 mmols) and 2-mercaprbenzoxzole (45 mg, 0.3 mmol), and stirred for 1.5 hours at 80° C. The mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline in that order, and dried with anhydrous sodium sulfate, and the solvent was evaporated. And the resulting crystals were recrystallized from hexane-ether, and colorless needle-like crystals 106 mg (yield: 90%) of the intended product as crystals.

Workup

  1. temperaturecooling in ice bath
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 1N-HCl
  5. dry with materialan aqueous saturated solution of sodium hydrogencarbonate, water, and saturated saline in that order, and dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThen, the resulting solid was recrystallized from hexan-ether

Sources & evidence

ORD record
ord-35a2764385bb4214acac04ea15f4fb91
Source dataset
uspto-grants-2001_03
Patent number
US06204278B1

Reaction notes

Loading…