2,4-Difluoroaniline → HCID 22013907, compound

HRID 1532710Notes

Reaction equation

HRID 1532710 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[F:22][C:23]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:24]=1[NH2:25].[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41](O)=[O:42]>CN(C=O)C>[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([NH:25][C:24]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=1[F:22])=[O:42]

Participants

6

Reactant 4

HCID 97092,4-DifluoroanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 14271210-Bromodecanoic Acid

Product 1

HCID 22013907HCID 22013907, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC (990 mg, 5.2 mmols) and HOBt (698 mg, 5.2 mmols) were added to a DMF (10 ml) solution of 2,4-difluoroaniline (1.29 g, 10 mmols) and 10-bromodecanoic acid (1.18 g, 4.7 mmols), and stirred at room temperature for 15 hours. The reaction mixture was extracted with ether. 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=10/1), and the resulting crystals were recrystallized from ether-hexane to obtain 763 mg (yield: 45%) of 10-bromo-N-(2,4-difluorophenyl)decanamide as colorless needle-like crystals.

Workup

  1. extractionThe reaction mixture was extracted with ether
  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=10/1)
  6. customthe resulting crystals were recrystallized from ether-hexane

Sources & evidence

ORD record
ord-1f890a95356f45aeaef7bf54d2808598
Source dataset
uspto-grants-2001_03
Patent number
US06204278B1

Reaction notes

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