Water → 2-[(3,5-Dimethylphenyl)thio]-6-nitrobenzonitrile

HRID 835

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HRID 835 반응식
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.C([O-])([O-])=O.[K+].[K+].[CH3:21][C:22]1[CH:23]=[C:24]([SH:29])[CH:25]=[C:26]([CH3:28])[CH:27]=1.O>CN(C=O)C>[CH3:21][C:22]1[CH:23]=[C:24]([S:29][C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=2[C:6]#[N:7])[CH:25]=[C:26]([CH3:28])[CH:27]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1175483,5-DimethylbenzenethiolHCID 520718Dinitrobenzonitrile

생성물 1

HCID 106130552-[(3,5-Dimethylphenyl)thio]-6-nitrobenzonitrile수율 73,011.203%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

A mixture of 2,6-dinitrobenzonitrile (1.4 g 7.2 mmol) and K2CO3 (1.1 g, 7.9 mmol) in 10 ml of DMF was chilled to 0° C. A solution of 3,5-dimethylthiophenol (1.1 g 0.0079 mmol) in 10 ml of DMF, was added dropwise over 30 min with stirring under nitrogen. After stirring an additional 30 min, the reaction mixture was poured into 150 ml of water and stirred for 1 hr. The solid was collected by vacuum filtration. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 1.64 g (80%) of 2-[(3,5-dimethylphenyl)thio]-6-nitrobenzonitrile: mp 155°-156° C.

후처리

  1. stirringAfter stirring an additional 30 min
  2. stirringstirred for 1 hr
  3. filtrationThe solid was collected by vacuum filtration

출처 및 근거

ORD 기록
ord-942c876021324f25bb9887685a674993
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723452

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