4-Methoxybenzylamine → HCID 59184872, compound

HRID 426230Notes

Reaction equation

HRID 426230 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>CS(C)=O.CCOCC>[F:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 5872043,5-Difluorobenzonitrile

Product 1

HCID 59184872HCID 59184872, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3,5-difluoro-benzonitrile (2.78 g, 20 mmol) and p-methoxybenzyl amine (5.74 ml, 44 mmol) in DMSO (20 ml) was stirred for 8 hr. in an oil bath (100-110° C.). After cooling to room temperature, the mixture was diluted with ether, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA: hexane (from 1:13 to 1:10)) to afford 3.92 g (76%) of a white solid. m.p. 93-94° C.; 1H NMR (200 MHz, CDCl3) δ 3.61 (3H, s), 4.04 (2H, s); 4.16 (1H, br. s), 6.27 (1H, m), 6.42-6.47 (2H, m), 6.69 (2H, d, J=7.2 Hz), 7.06 (2H, d, J=7.2 Hz).

Workup

  1. custom(100-110° C.)
  2. washwashed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent, EA: hexane (from 1:13 to 1:10))

Sources & evidence

ORD record
ord-ac3d91d5d95e4345940cdfc361bdb47b
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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