Sodium Iodide → HCID 18681108, compound

HRID 276074Notes

Reaction equation

HRID 276074 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:10]([CH3:11])=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:5]=2[N:6]=1.[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH2:19]Cl.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH2:19][N:6]1[C:5]2[CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[C:10]([CH3:11])[C:4]=2[N:3]=[C:2]1[CH3:1]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 178497593HCID 178497593, compound

Product 1

HCID 18681108HCID 18681108, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture containing 0.900 g of 2,4-dimethyl-6-methoxycarbonylbenzimidazole, 1.20 g of 2,4-dichlorobenzyl chloride, 0.200 g of sodium iodide, 0.610 g of potassium carbonate and 4 ml of N,N-dimethylformamide was stirred at 80° C. for 16 hours. After the organic solvent was distilled off under reduced pressure, the residue was extracted with ethyl acetate and with water. The organic layer was concentrated, and was crystallized with the addition of hexane. The crystals were separated through filtration, and were dried to give 1.08 g of 1-(2,4-dichlorobenzyl)-2,4-dimethyl-6-methoxycarbonylbenzimidazole (353).

Workup

  1. distillationAfter the organic solvent was distilled off under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate and with water
  3. concentrationThe organic layer was concentrated
  4. customwas crystallized with the addition of hexane
  5. customThe crystals were separated through filtration
  6. customwere dried

Sources & evidence

ORD record
ord-44981391e647483bba679268e910a0e9
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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