Water → N-(4-methoxybenzyl)-2-chloro-6-methylbenzamide

HRID 518261Notes

Reaction equation

HRID 518261 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:13]=1[C:14](Cl)=[O:15].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:14](=[O:15])[C:13]2[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:12]=2[Cl:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 754524-MethoxybenzylamineHCID 223820402-Chloro-6-methylbenzoyl chloride

Product 1

HCID 71270345N-(4-methoxybenzyl)-2-chloro-6-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-methoxyphenyl)methanamine (264 g, 2.4 mol, 1.eq) in DCM (1800 mL), a solution of 2-chloro-6-methylbenzoyl chloride (340) in DCM (150 mL) was added dropwise while keeping the reaction temperature between 25° C. to 40° C. The resulting mixture was stirred at RT for 2 h, and then water (600 mL) was added. The organic layer was separated, washed with water (2×300 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was slurried in petroleum ether (300 mL) and stirred at RT for 30 min. The solid was collected by filtration and further dried in vacuo to afford N-(4-methoxybenzyl)-2-chloro-6-methylbenzamide (341).

Workup

  1. custombetween 25° C. to 40° C
  2. customThe organic layer was separated
  3. washwashed with water (2×300 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. stirringstirred at RT for 30 min
  8. filtrationThe solid was collected by filtration
  9. customfurther dried in vacuo

Sources & evidence

ORD record
ord-4e1c1198135a4e9e9989ed9e9877cff8
Source dataset
uspto-grants-2015_08
Patent number
US09115141B2

Reaction notes

Loading…