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HRID 1076289作成日:2026年10月27日

Benzene → Diethylformamide

https://huagongshe.com/reaction/1076289

反応式

関与物質

役割名称HCID仕込み量
反応物BenzeneHCID 241—
反応物1,4-DichlorobenzeneHCID 4685—
反応物Thionyl ChlorideHCID 24386—
反応物Ethanolamine HydrochlorideHCID 74819—
溶媒1,2-DichloroethaneHCID 11—
溶媒WaterHCID 962—
溶媒PyridineHCID 1049—
溶媒TolueneHCID 1140—
溶媒DimethylformamideHCID 6228—
溶媒O-XyleneHCID 7237—
溶媒ChlorobenzeneHCID 7964—
溶媒N-methyl-2-pyrrolidoneHCID 13387—
生成物DiethylformamideHCID 12051—
生成物2-Chloroethylamine hydrochlorideHCID 9793737—

反応手順

The reaction between monoethanolamine hydrochloride and thionylchloride is carried out in a molar ratio of 1:1.05 - 1.2, at 50° to 100°C. for 3 to 10 hours, in water-insoluble solvents such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene and 1,2-dichloroethane, and in the presence of a catalyst such as dimethylformamide, diethylformamide, N-methylpyrrolidone and pyridine to obtain 2-chloroethylamine hydrochloride with good purity. And, as a result of further investigation, the inventors have found that sulfur dioxide which is produced as a by-product in the course of the chlorination acts as a negative catalyst in the subsequent amidation, i.e. the reaction between the sulfonylhalide (II) and the resulting 2-chloroethyl-amine or salts thereof, and that the yield can be much increased by forcing sulfur dioxide to be removed.

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US03956385
出典データセットuspto-grants-1976_05
ORD IDord-1a7200b06eb749e6ba48dea2864c888b
出典メモuspto-grants-1976_05