2-Chloroaniline → Imidazolidine, 2-(2-chlorophenylimino)-

HRID 1577140

反応式

HRID 1577140 の反応式
S(=O)(=O)(O)O.Cl[C:7]1[NH:8][CH2:9][CH2:10][N:11]=1.[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].[OH-].[Na+]>CO.O>[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[N:15]=[C:7]1[NH:8][CH2:9][CH2:10][NH:11]1

参加物

6

反応物 3

HCID 72402-ChloroanilineHCID 14798Sodium HydroxideHCID 125033982-Chloroimidazoline sulfate

生成物 1

HCID 138342Imidazolidine, 2-(2-chlorophenylimino)-収率 48%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To 2-chloroimidazoline bisulfate (60.0 g, 300 mmoles) in methanol (600 ml) and water (150 ml) is added with stirring 2-chloroaniline (81.1 g, 67 ml, 636 mmoles). The heterogeneous mixture is stirred at ambient temperature overnight. After 20 hours the mixture is poured into ice water, made strongly alkaline with sodium hydroxide and extracted with dichloromethane twice. The organic extracts are washed once with water and once with saturated sodium chloride solution and then extracted with 2 N acetic acid (2×1 liter). The combined acid extracts are backwashed with dichloromethane, made strongly alkaline with sodium hydroxide, and once again extracted with dichloromethane twice. The dichloromethane extracts are combined, washed with water and then sodium chloride solution and finally dried and evaporated in vacuo. The solid residue (31 g) is dissolved in hot toluene, filtered, and diluted with hexane (total volume 3 liters). Colorless crystals separate which are filtered, washed with hexane and air-dried, to give 28.2 g of 2-(2-chlorophenylimino)imidazolidine, m.p. 133°-134° C.

後処理

  1. extractionextracted with dichloromethane twice
  2. washThe organic extracts are washed once with water and once with saturated sodium chloride solution
  3. extractionextracted with 2 N acetic acid (2×1 liter)
  4. extractiononce again extracted with dichloromethane twice
  5. washwashed with water
  6. dry with materialsodium chloride solution and finally dried
  7. customevaporated in vacuo
  8. dissolutionThe solid residue (31 g) is dissolved in hot toluene
  9. filtrationfiltered
  10. additiondiluted with hexane (total volume 3 liters)
  11. customColorless crystals separate which
  12. filtrationare filtered
  13. washwashed with hexane
  14. customair-dried

出典と根拠

ORDレコード
ord-2f73aa793ac34c45ae2ae5c5f10b475b
出典データセット
uspto-grants-1981_09
特許番号
US04287201

関連ノート

読み込み中…