HRID573956

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6547

Azobisisobutyronitrile

C8H12N4

HCID67184

1-Bromopyrrolidine-2,5-dione

C4H4BrNO2

$结构：Cc1ccc(C(C)C)c(N2C(=O)CS/C2=N\C(=O)NCCc2ccc(-c3ncn(-c4ccc(OC(F)(F)F)cc4)n3)cc2)c1$

HCID78319090

未命名化合物

PRODUCTS

生成物

$结构：Cc1ccc(C(C)C)c(N2C(=O)CS/C2=N\C(=O)NCC(Br)c2ccc(-c3ncn(-c4ccc(OC(F)(F)F)cc4)n3)cc2)c1$

HCID90412728

未命名化合物

收率 21.8%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID5943

Carbon tetrachloride

CCl4

PROCEDURE

实验过程

To a dry round-bottomed flask (20 mL) equipped with a magnetic stirrer and a reflux condenser were added (Z)-1-(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)urea (F5) (0.20 g, 0.32 mmol), carbon tetrachloride (1 mL), N-bromosuccinimide (0.057 g, 0.32 mmol), and azobisisobutyronitrile (0.0053 g, 0.032 mmol). The reaction was heated to reflux for 2 hours. The reaction was cooled. Purification by flash column chromatography using 0-100% ethyl acetate/hexanes as eluent provided the title compound as a yellow oil (0.049 g, 21%).

WORKUP

后处理

customTo a dry round-bottomed flask (20 mL) equipped with a magnetic stirrer and a reflux condenser
temperatureThe reaction was heated
temperatureto reflux for 2 hours
temperatureThe reaction was cooled
customPurification by flash column chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cbc8e044a0b845eaa7b57b76be534175
来源数据集: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09029560B2
来源说明: uspto-grants-2015_05

反应 SMILES

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[N:11]1[C:15](=[O:16])[CH2:14][S:13]/[C:12]/1=[N:17]\[C:18]([NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:33]=[CH:32][N:31]([C:34]3[CH:39]=[CH:38][C:37]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:36][CH:35]=3)[N:30]=2)=[CH:25][CH:24]=1)=[O:19])([CH3:3])[CH3:2].[Br:45]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:45][CH:22]([C:23]1[CH:24]=[CH:25][C:26]([C:29]2[N:33]=[CH:32][N:31]([C:34]3[CH:35]=[CH:36][C:37]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:38][CH:39]=3)[N:30]=2)=[CH:27][CH:28]=1)[CH2:21][NH:20][C:18](/[N:17]=[C:12]1\[S:13][CH2:14][C:15](=[O:16])[N:11]\1[C:5]1[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])=[O:19]