HRID1448504

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

结构：Nc1ccc(S(=O)(=O)O)c2cc(S(=O)(=O)O)cc(S(=O)(=O)O)c12

HCID87355

8-Aminonaphthalene-1,3,5-trisulphonic acid

C10H9NO9S3

结构：O=C([O-])C1=NN(c2ccc(S(=O)(=O)[O-])cc2)C(=O)C1N=Nc1ccc(S(=O)(=O)[O-])cc1.[Na+].[Na+].[Na+]

HCID164825

未命名化合物

HCID517045

Sodium Acetate

C2H3NaO2

HCID3016522

4-Methyl-2-nitrobenzoyl chloride

C8H6ClNO3

2 次

HCID23665404

Acetic acid, sodium salt, trihydrate

C2H9NaO5

PRODUCTS

生成物

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

HCID57288108

未命名化合物

收率 872.9%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID3283

Diethyl Ether

C4H10O

PROCEDURE

实验过程

To a stirred solution of 22.5 g of 8-amino-1,3,5-naphthalenetrisulfonic acid, trisodium salt in 160 ml of water is added 11.0 g of the preceding product with a small amount of ether. Stirring is continued, and after one hour 1.0 g of sodium acetate trihydrate and 1.0 g of 3-nitro-p-toluoyl chloride are added. The mixture is stirred an additional 3 hours and the above addition of sodium acetate and 3-nitro-p-toluoyl chloride is repeated. The mixture is stirred an additional hour, acidified to Congo Red indicator paper with hydrochloric acid and filtered. The filtrate is neutralized with sodium hydroxide, concentrated, dissolved in 50 ml of water and added to one liter of ethanol with stirring for 16 hours. The solid is filtered and forms a gel on washing with ethanol. The gel is dissolved in water and evaporated. The residue is dissolved in 35 ml of hot water and 320 ml of absolute ethanol is added with stirring. The mixture solidifies and water is added to allow filtration. The solid is washed with ether and dried in vacuo. The filtrate is treated by stirring with one liter of ethanol, the separated solid is collected, washed with ether, and dried to yield a combined total of 23.9 g of 8-(3-nitro-p-toluamido)-1,3,5-naphthalenetrisulfonic acid, trisodium salt.

WORKUP

后处理

stirringThe mixture is stirred an additional 3 hours
stirringThe mixture is stirred an additional hour
filtrationfiltered
concentrationconcentrated
dissolutiondissolved in 50 ml of water
additionadded to one liter of ethanol
stirringwith stirring for 16 hours
filtrationThe solid is filtered
washforms a gel on washing with ethanol
dissolutionThe gel is dissolved in water
customevaporated
dissolutionThe residue is dissolved in 35 ml of hot water
addition320 ml of absolute ethanol is added
stirringwith stirring
additionwater is added
filtrationfiltration
washThe solid is washed with ether
customdried in vacuo
additionThe filtrate is treated
stirringby stirring with one liter of ethanol
customthe separated solid is collected
washwashed with ether
customdried

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6610eb9395544218981b9114b6b5fefb
来源数据集: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04180587
来源说明: uspto-grants-1979_12

反应 SMILES

[NH2:1][C:2]1[C:11]2[C:10]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9][C:8]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:7][C:6]=2[C:5]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:4][CH:3]=1.C1C(N=NC2C(=O)N(C3C=CC(S([O-])(=O)=O)=CC=3)N=C2C([O-])=O)=CC=C(S([O-])(=O)=O)C=1.[Na+].[Na+].[Na+].O.O.O.C([O-])(=O)C.[Na+].[N+:66]([C:69]1[CH:70]=[C:71]([CH3:78])[CH:72]=[CH:73][C:74]=1[C:75](Cl)=[O:76])([O-:68])=[O:67].C([O-])(=O)C.[Na+].Cl>O.CCOCC>[N+:66]([C:69]1[CH:70]=[C:71]([CH3:78])[CH:72]=[CH:73][C:74]=1[C:75]([NH:1][C:2]1[C:11]2[C:10]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:9][C:8]([S:16]([OH:19])(=[O:17])=[O:18])=[CH:7][C:6]=2[C:5]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:4][CH:3]=1)=[O:76])([O-:68])=[O:67]