1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → 2-((3,4-Dichloroanilino)methyl)-2-imidazoline hydrochloride

HRID 67086

反応式

HRID 67086 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[NH:5][CH2:6][C:7]#[N:8].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](N)[CH2:25][NH2:26]>ClC1C=CC=CC=1Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[NH:5][CH2:6][C:7]1[NH:26][CH2:25][CH2:24][N:8]=1

参加物

4

反応物 2

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 128325593,4-Dichloroanilinoacetonitrile

生成物 1

HCID 205285022-((3,4-Dichloroanilino)methyl)-2-imidazoline hydrochloride収率 61.8%

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒

実験手順

A mixture of 30.15 g of 3,4-dichloroanilinoacetonitrile and 35.0 g of ethylenediamine p-toluenesulfonate in 110 ml of 1,2-dichlorobenzene was heated at reflux temperature under a small flow of nitrogen for 1.5 hours. The reaction mixture was then cooled and washed with water. The 1,2-dichlorobenzene was concentrated under vacuum and the remaining residue was put in solution in CH2Cl2 and shaken with dilute sodium hydroxide. The CH2Cl2 layer was separated and treated with diatomaceous earth and activated charcoal and then filtered. The filtrate was concentrated to dryness under vacuum and the black gummy residue which remained put in solution in isopropyl alcohol. Gaseous HCl was bubbled through the solution resulting in crystal formation. The mixture was cooled and filtered to obtain the product. Recrystallization from absolute ethanol gave 13.0 g of purified 2-((3,4-dichloroanilino)methyl)-2-imidazoline hydrochloride as tan crystals, m.p. 221°-223° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux temperature under a small flow of nitrogen for 1.5 hours
  3. temperatureThe reaction mixture was then cooled
  4. washwashed with water
  5. concentrationThe 1,2-dichlorobenzene was concentrated under vacuum
  6. customThe CH2Cl2 layer was separated
  7. additiontreated with diatomaceous earth and activated charcoal
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated to dryness under vacuum
  10. customGaseous HCl was bubbled through the solution
  11. customresulting in crystal formation
  12. temperatureThe mixture was cooled
  13. filtrationfiltered
  14. customto obtain the product
  15. customRecrystallization from absolute ethanol

出典と根拠

ORDレコード
ord-60abf03fdbeb4fea8dcda807345d0d3e
出典データセット
uspto-grants-1982_08
特許番号
US04344958

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