Sodium hydride → 2-Chloro-5-iodo-N,N-bis(4-methoxybenzyl)aniline

HRID 2402345Notes

Reaction equation

HRID 2402345 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:5]=1[NH2:6].Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>CN(C=O)C>[Cl:3][C:4]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:5]=1[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 398719712-Chloro-5-iodoaniline

Product 1

HCID 708733002-Chloro-5-iodo-N,N-bis(4-methoxybenzyl)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Under argon, 12.62 g (316.16 mmol, 60% in mineral oil) of sodium hydride were suspended in 250 ml of abs. DMF and cooled to 0° C. 32 g (126.3 mmol) of 2-chloro-5-iodoaniline, dissolved in 80 ml of abs. DMF, were then slowly added dropwise, and the mixture was stirred at 0° C. for 30 min. 41 ml (303 mmol) of 1-(chloromethyl)-4-methoxybenzene were then slowly added to the reaction mixture, and the mixture was subsequently warmed to room temperature. The mixture was stirred at RT overnight and then carefully poured into 150 ml of ice-water. The organic phase was separated off, and the aqueous phase was then extracted three more times with diethyl ether. The combined organic phases were dried over magnesium sulphate. After filtration, the solvent was removed under reduced pressure. The crude product obtained was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1). This gave 59 g of the title compound (94% of theory).

Workup

  1. temperaturethe mixture was subsequently warmed to room temperature
  2. stirringThe mixture was stirred at RT overnight
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was then extracted three more times with diethyl ether
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-07f968dbd9d24679a1ca9d692cc5398c
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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