Sodium Iodide → HCID 18681108, compound

HRID 1699644Notes

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

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,4-dimethyl-6-methoxycarbonylbenzimidazole (0.900 g), 2,4-dichlorobenzyl chloride (1.20 g), sodium iodide (0.200 g), potassium carbonate (0.610 g) and N,N-dimethylformamide (4 ml) is stirred for 16 hours at 80° C. After removing the organic solvent through evaporation under reduced pressure, ethyl acetate and water are added and extraction is performed. The organic layer is concentrated, hexane is added and it is crystallized. The crystals are separated through filtration, dried and thus, 1-(2,4-dichlorobenzyl)-2,4-dimethyl-6-methoxycarbonylbenzimidazole (1.08 g) is obtained. 1H-NMR (CDCl3, δ): 2.58 (3H, s), 2.71 (3H, s), 3.90 (3H, s), 5.39 (2H, s), 6.30 (1H, d, J=8.4 Hz), 7.07 (1H, dd, J=8.4 and 2.0 Hz), 7.49 (1H, d, J=2.0 Hz), 7.75 (1H, s), 7.81 (1H, s).

Workup

customAfter removing the organic solvent
customthrough evaporation under reduced pressure, ethyl acetate and water
additionare added
extractionextraction
concentrationThe organic layer is concentrated
additionhexane is added
customit is crystallized
customThe crystals are separated through filtration
customdried

Sources & evidence

ORD record: ord-f9166b44929746148dff7d10b767add2
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348032B1

Reaction notes

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