Benzene → Diethylformamide

HRID 1076289

反応式

HRID 1076289 の反応式
Cl.C([CH2:4][NH2:5])O.S(Cl)([Cl:8])=[O:7].[CH:10]1[CH:15]=CC=CC=1.[CH:16]1[C:21](Cl)=CC=[C:18]([Cl:23])[CH:17]=1>O.N1C=CC=CC=1.CN1CCCC1=O.CN(C)C=O.ClCCCl.ClC1C=CC=CC=1.C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1>[CH2:16]([N:5]([CH2:15][CH3:10])[CH:4]=[O:7])[CH3:21].[ClH:8].[Cl:23][CH2:18][CH2:17][NH2:5]

参加物

14

反応物 4

HCID 241BenzeneHCID 46851,4-DichlorobenzeneHCID 24386Thionyl ChlorideHCID 74819Ethanolamine Hydrochloride

生成物 2

HCID 12051DiethylformamideHCID 97937372-Chloroethylamine hydrochloride

試薬・触媒・溶媒 8

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 7237O-Xylene溶媒HCID 7964Chlorobenzene溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-1a7200b06eb749e6ba48dea2864c888b
出典データセット
uspto-grants-1976_05
特許番号
US03956385

関連ノート

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