Dimethylformamide → HCID 154041401, compound

HRID 1885042Notes

Reaction equation

HRID 1885042 reaction equation
[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([CH:9]=[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]/[C:11]/2=[N:20]\[OH:21])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>ClCCl.O>[CH2:24]([O:21]/[N:20]=[C:11]1/[C:10](=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:23][CH:22]=2)[C:19]2[C:14]([CH2:13][CH2:12]/1)=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 154041398HCID 154041398, compound

Product 1

HCID 154041401HCID 154041401, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
97.5 °C

Procedure

(E)-1-(4-methanesulfonyl-benzylidene)-3,4-dihydro-1H-naphthalene-2-one oxime (25 mg, 0.076 mmol), benzyl bromide (0.022 ml, 0.18 mmol) and potassium carbonate (0.032 g, 0.23 mmol) were added into dimethylformamide (1.0 ml). Then, the solution was stirred at 95-100° C. for 48 hours, and cooled to room temperature. Again, water and dichloromethane were added, and an organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to remove organic solvent. The residue was purified through silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3, v/v). As a result, 26 mg of the present compound (productive yield 82%) was obtained as a white solid crystal.

Workup

  1. temperaturecooled to room temperature
  2. customan organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto remove organic solvent
  7. customThe residue was purified through silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-fd81f940e5354b86997f35f51f17a8c5
Source dataset
uspto-grants-2004_07
Patent number
US06768019B2

Reaction notes

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