HRID411612

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7398

Benzenesulfonyl chloride, 4-chloro-

C6H4Cl2O2S

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID5360545

Sodium

结构：COc1ccnc(CS(=O)c2nc3cc(OC(F)F)ccc3[nH]2)c1OC

HCID178493215

未命名化合物

PRODUCTS

生成物

结构：COc1ccnc(CS(=O)c2nc3cc(OC(F)F)ccc3n2S(=O)(=O)c2ccc(Cl)cc2)c1OC

HCID15895226

未命名化合物

结构：COc1ccnc(CS(=O)c2nc3ccc(OC(F)F)cc3n2S(=O)(=O)c2ccc(Cl)cc2)c1OC

HCID18541222

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

CONDITIONS

反应条件

温度: 4 °C

PROCEDURE

实验过程

5-Difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole, sodium salt sesquihydrate (432 mg, 1 mmole) was suspended in 30 ml of dichloromethane in the presence of anhydrous sodium carbonate (100 mg). 4-Chlorobenzenesulfonyl chloride (211 mg, 1 mmole) was added to the suspension and stirred at 4° C. overnight. The organic layer was separated by filtration and concentrated under reduced pressure. The residual solid was crystallized from dichloromethane-ethyl ether-heptane. 417 mg of isomer, 1-(4-chlorobenzenesulfonyl)-5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole and 1-(4-chlorobenzenesulfonyl)-6-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole (5:4 ratio by NMR), was obtained. Yield 74.5% M.P. 82-83° C.

WORKUP

后处理

customThe organic layer was separated by filtration
concentrationconcentrated under reduced pressure
customThe residual solid was crystallized from dichloromethane-ethyl ether-heptane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e431d9d8b7744a37b059cd7d98da4326
来源数据集: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06559167B1
来源说明: uspto-grants-2003_05

反应 SMILES

[F:1][CH:2]([F:26])[O:3][C:4]1[CH:25]=[CH:24][C:7]2[NH:8][C:9]([S:11]([CH2:13][C:14]3[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][N:15]=3)=[O:12])=[N:10][C:6]=2[CH:5]=1.[Na].C(=O)([O-])[O-].[Na+].[Na+].[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>ClCCl>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([N:8]2[C:7]3[CH:24]=[CH:25][C:4]([O:3][CH:2]([F:1])[F:26])=[CH:5][C:6]=3[N:10]=[C:9]2[S:11]([CH2:13][C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][N:15]=2)=[O:12])(=[O:43])=[O:42])=[CH:37][CH:36]=1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([N:10]2[C:6]3[CH:5]=[C:4]([O:3][CH:2]([F:1])[F:26])[CH:25]=[CH:24][C:7]=3[N:8]=[C:9]2[S:11]([CH2:13][C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][N:15]=2)=[O:12])(=[O:43])=[O:42])=[CH:37][CH:36]=1