Chlorosulfonic acid → HCID 18680859, compound

HRID 1699642Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:14].[Cl:20][S:21](O)(=[O:23])=[O:22]>>[Cl:20][S:21]([C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:6]([CH3:14])[N:5]([CH2:4][C:3]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:2]=3[Cl:1])[C:9]=2[CH:10]=1)(=[O:23])=[O:22]

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

HCID 932278HCID 932278, compound

Product 1

HCID 18680859HCID 18680859, compound

Conditions

Temperature: 80 °C

Procedure

In an ice bath, 1-(2,4-dichlorobenzyl)-2-methylbenzimidazole (4.00 g) is added to chlorosulfonic acid (20 ml) and the solution is stirred for 24 hours at room temperature and at 1.5 hours at 80° C. The reaction solution is poured into ice water, precipitated gummy solids are separated through filtration, and thus, a mixture of 5-chlorosulfonyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole and 6-chlorosulfonyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole is obtained. This material is immediately used for the following reaction.

Workup

customprecipitated gummy solids
customare separated through filtration
additionthus, a mixture of 5-chlorosulfonyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole

Sources & evidence

ORD record: ord-4f8fbf99ae19403085034ae67b8edb90
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06348032B1

Reaction notes

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