HRID1368648

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14797

Potassium hydroxide

HKO

HCID139882

4-t-Butylbenzenesulfonyl chloride

C10H13ClO2S

结构：Cc1ccc(-c2c(OCCOc3ccc(F)cc3)nn(C)c2N)cc1

HCID23400312

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(-c2c(OCCOc3ccc(F)cc3)nn(C)c2N(S(=O)(=O)c2ccc(C(C)(C)C)cc2)S(=O)(=O)c2ccc(C(C)(C)C)cc2)cc1

HCID22281892

未命名化合物

收率 79.7%

AUXILIARIES

试剂、催化剂与溶剂

结构：CCCC[N+](CCCC)(CCCC)CCCC.O=S(=O)([O-])O

催化剂HCID94433

未命名化合物

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To 3-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-ylamine (Preparation 26) (105mg) in dichloromethane (20ml) at room temperature was added 4-tert-butylbenzenesulfonyl chloride (2 g), tetrabutylammonium hydrogen sulfate (75 mg) and potassium hydroxide (690 mg), the mixture was sonicated for 3 hrs. The reaction was partitioned between 2N aqueous hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, then brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel, eluting with a solvent gradient of pentane:ethyl acetate (39:1 to 4:1), to yield the title compound as a glass (180 mg).

WORKUP

后处理

customthe mixture was sonicated for 3 hrs
customThe reaction was partitioned between 2N aqueous hydrochloric acid and ethyl acetate
customThe organic layer was separated
washwashed with water
dry with materialbrine, dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography
washeluting with a solvent gradient of pentane:ethyl acetate (39:1 to 4:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-870fd1bf63ef4f04a5e2fd29ed1cb234
来源数据集: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06573270B1
来源说明: uspto-grants-2003_06

反应 SMILES

[F:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][CH2:8][O:9][C:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)=[C:13]([NH2:22])[N:12]([CH3:23])[N:11]=2)=[CH:4][CH:3]=1.[C:26]([C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27].[OH-:40].[K+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:26]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([N:22]([S:36]([C:33]2[CH:34]=[CH:35][C:30]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:31][CH:32]=2)(=[O:37])=[O:40])[C:13]2[N:12]([CH3:23])[N:11]=[C:10]([O:9][CH2:8][CH2:7][O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=3)[C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27]