Oxalyl chloride → 1-[3-(Chlorocarbonyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383969Notes

Reaction equation

HRID 1383969 reaction equation
[C:1]([CH:4]([CH3:26])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=2[N:9]=[C:8]1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(O)=[O:2].C(Cl)(=O)C([Cl:30])=O>C(Cl)Cl.CN(C)C=O>[Cl:30][C:1]([CH:4]([CH3:26])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=2[N:9]=[C:8]1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 211885121-(3-Carboxybutyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Product 1

HCID 211887451-[3-(Chlorocarbonyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazoleYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere at room temperature 1-[3-(carboxy)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (1.2 g, 3.2 mmol) was added in one portion to oxalyl chloride (5 ml) in methylene chloride (150 ml). After the material solubilized, one drop of N,N-dimethylformamide was added to initiate the reaction. Bubbling of the solution began and was visible for approximately fifteen minutes. The reaction mixture was stirred at room temperature for two hours. The reaction mixture was then concentrated under reduced pressure, reuslting in the formation of a white solid. The solid was triturated in 100 ml of hexanes, filtered and dried in a vacuum oven at 50° C. for one hours to yield the title product (1.3 g, 91%) as a white solid.

Workup

  1. customthe reaction
  2. customBubbling of the solution
  3. waitwas visible for approximately fifteen minutes
  4. concentrationThe reaction mixture was then concentrated under reduced pressure
  5. customThe solid was triturated in 100 ml of hexanes
  6. filtrationfiltered
  7. customdried in a vacuum oven at 50° C. for one hours

Sources & evidence

ORD record
ord-c5394ad2ab1e4f4abdaef35d4e0e5528
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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