HRID224337

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8476

Benzenesulfonyl chloride, 3-nitro-

C6H4ClNO4S

2 次

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID19660

Carbonate

CO3-2

结构：Cc1ccc(S(=O)(=O)Nc2ccc(S(=O)(=O)[O-])c3cc(S(=O)(=O)[O-])cc(S(=O)(=O)[O-])c23)c(N)c1.[Na+].[Na+].[Na+]

HCID131711510

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(S(=O)(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)c(NS(=O)(=O)c2cccc([N+](=O)[O-])c2)c1

HCID86736550

未命名化合物

收率 29.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

PROCEDURE

实验过程

To a stirred solution of 2.0 g of 8-(3-amino-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acid trisodium salt and 342 mg of anhydrous sodium carbonate in 10 ml of water is added 1.5 g of m-nitrobenzenesulfonyl chloride. The mixture is stirred for 16 hours. An additional 170 mg of anhydrous sodum carbonate is added followed by 750 mg of m-nitrobenzenesulfonyl chloride and the mixture is stirred for an additional 16 hours. The reaction mixture is evaporated and the residue dissolved in hot water. A product is precipitated on the addition of absolute ethanol. The product is collected, washed with ethanol and ether and dried. Additional product is collected from the filtrate and is washed and dried as above. The above fractions of product are combined and dissolved in water, then 2.5 ml of 5 N sodium hydroxide is added and the mixture is stirred for 30 minutes. The mixture is acidified with glacial acetic acid and evaporated. The residue is dissolved in hot water and precipitated with ethanol. The product is collected and washed twice with ethanol and ether and dried to yield 700 mg of 8-(3-m-nitrobenzenesulfonamido-p-toluenesulfonamido)-1,3,5-naphthalenetrisulfonic acid, trisodium salt.

WORKUP

后处理

stirringthe mixture is stirred for an additional 16 hours
customThe reaction mixture is evaporated
dissolutionthe residue dissolved in hot water
customA product is precipitated on the addition of absolute ethanol
customThe product is collected
washwashed with ethanol and ether
customdried
customAdditional product is collected from the filtrate
washis washed
customdried as above
dissolutiondissolved in water
addition2.5 ml of 5 N sodium hydroxide is added
stirringthe mixture is stirred for 30 minutes
customevaporated
dissolutionThe residue is dissolved in hot water
customprecipitated with ethanol
customThe product is collected
washwashed twice with ethanol and ether
customdried

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4247c53c9f7f43f59776d3d2a494b88f
来源数据集: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04231958
来源说明: uspto-grants-1980_11

反应 SMILES

[Na+].[Na+].[Na+].[NH2:4][C:5]1[CH:6]=[C:7]([CH3:37])[CH:8]=[CH:9][C:10]=1[S:11]([NH:14][C:15]1[C:24]2[C:23]([S:25]([O-:28])(=[O:27])=[O:26])=[CH:22][C:21]([S:29]([O-:32])(=[O:31])=[O:30])=[CH:20][C:19]=2[C:18]([S:33]([O-:36])(=[O:35])=[O:34])=[CH:17][CH:16]=1)(=[O:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+].[N+:44]([C:47]1[CH:48]=[C:49]([S:53](Cl)(=[O:55])=[O:54])[CH:50]=[CH:51][CH:52]=1)([O-:46])=[O:45].C(=O)([O-])[O-]>O>[N+:44]([C:47]1[CH:48]=[C:49]([S:53]([NH:4][C:5]2[CH:6]=[C:7]([CH3:37])[CH:8]=[CH:9][C:10]=2[S:11]([NH:14][C:15]2[C:24]3[C:23]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:22][C:21]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:20][C:19]=3[C:18]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:17][CH:16]=2)(=[O:13])=[O:12])(=[O:55])=[O:54])[CH:50]=[CH:51][CH:52]=1)([O-:46])=[O:45]