HRID1970799

反应详情

EQUATION

反应方程式

REACTANTS

反应物

反应SMILES：O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1

HCID7404

Benzenesulfonyl chloride, 4-nitro-

C6H4ClNO4S

2 次

HCID516892

Sodium Bicarbonate

CHNaO3

反应SMILES：CC(=O)Oc1ccc(-c2cnc(N)c(Cc3ccccc3)n2)cc1

HCID67003552

未命名化合物

PRODUCTS

产物

反应SMILES：CC(=O)Oc1ccc(-c2cnc(N(S(=O)(=O)c3ccc([N+](=O)[O-])cc3)S(=O)(=O)c3ccc([N+](=O)[O-])cc3)c(Cc3ccccc3)n2)cc1

HCID46866264

未命名化合物

收率 52.1%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

Under an argon atmosphere, 5-(4-acetoxyphenyl)-2-amino-3-benzylpyrazine (c-19) (140 mg, 438 μmol) was dissolved in pyridine (2 mL) and to this was added 4-(dimethylamino)pyridine (6.0 mg, 49 μmol). To this was added p-nitrobenzenesulfonyl chloride (293 mg, 1.32 mmol) while stirring at room temperature and stirred for 1.5 h at the same temperature. To this was further added p-nitrobenzenesulfonyl chloride (195 mg, 880 μmol) and stirred for 17 h. To this was added saturated aqueous solution of sodium bicarbonate to stop the reaction and the product was extracted twice with dichloromethane. The organic layer was washed once with water and once with saturated aqueous solution of sodium sulfate and then dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (24 g, n-hexane/ethyl acetate=4/1→3/1→7/3→ethyl acetate alone) to give 5-(4-acetoxyphenyl)-3-benzyl-2-bis(4-nitrophenylsulfonyl)aminopyrazine (c-40) as a dark brown solid (157 mg, 52.1%). Rf=0.62 (n-hexane/ethyl acetate=3/2). Mp. 227-229.5° C. (dec.). UV (MeOH, 0.3% DMSO) λmax (log ε) 309 (3.99), 258 (4.21). 1H NMR (400 MHz, DMSO-d6) δ 2.30 (s, 3H), 4.22 (s, 2H), 7.19-7.27 (m, 1H), 7.29-7.35 (m, 6H), 8.05-8.10 (AA′BB′, 4H), 8.14-8.19 (AA′BB′, 2H), 8.39-8.44 (AA′BB′, 4H), 9.13 (s, 1H). 13C NMR. (75.5 MHz, DMSO-d6) δ 20.9, 38.0, 122.8 (2C), 124.8 (2C×2), 126.6, 128.3 (2C), 128.7 (2C), 129.6 (2C), 130.7 (2C×2), 131.9, 137.3, 139.8, 140.3, 142.1 (1C×2), 151.1 (1C×2), 151.9, 152.7, 156.2, 169.0. I,R (KBr, cm−1) 548, 598, 617, 687, 737, 775, 810, 854, 880, 897, 916, 935, 1013, 1165, 1180, 1206, 1315, 1348, 1368, 1385, 1404, 1418, 1435, 1530, 1603, 1755, 3107. HRMS (FAR) m/z 690.0975 (M+H, C31H24N5O10S2 requires 690.0965).

WORKUP

后处理

stirringstirred for 1.5 h at the same temperature
stirringstirred for 17 h
customthe reaction
extractionthe product was extracted twice with dichloromethane
washThe organic layer was washed once with water and once with saturated aqueous solution of sodium sulfate
dry with materialdried over anhydrous sodium sulfate
customAfter removing anhydrous sodium sulfate
filtrationby filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography (24 g, n-hexane/ethyl acetate=4/1→3/1→7/3

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-e30b100d1a824fa5a429c6544b00ed2a
来源数据集: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US08431525B2
来源说明: uspto-grants-2013_04

反应SMILES

[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([NH2:17])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([O-:27])=[O:26].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([N:17]([S:34]([C:31]3[CH:30]=[CH:29][C:28]([N+:25]([O-:27])=[O:26])=[CH:33][CH:32]=3)(=[O:35])=[O:36])[S:34]([C:31]3[CH:32]=[CH:33][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=3)(=[O:36])=[O:35])=[N:15][CH:16]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]