1,2-Dichlorobenzene → 2-((4-Chlorophenoxy)methyl)-2-imidazoline hydrochloride

HRID 66729

反応式

HRID 66729 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:23](N)[CH2:24][NH2:25].ClC1C=CC=CC=1Cl>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]2[NH:25][CH2:24][CH2:23][N:9]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 72391,2-DichlorobenzeneHCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 3064442-(4-Chlorophenoxy)acetonitrile

生成物 1

HCID 205290632-((4-Chlorophenoxy)methyl)-2-imidazoline hydrochloride収率 148.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
178 °C

実験手順

A mixture of 25.1 g of 4-chlorophenoxyacetonitrile, 35.0 g of ethylenediamine p-toluenesulfonate and 112.5 ml of 1,2-dichlorobenzene was heated with stirring in a 500 ml round-bottomed three-necked flask at reflux (178° C.) for 1.0 hour. The reaction mixture was cooled, then diluted with methylene chloride and filtered. The crystals that were obtained were dried in a vacuum oven. The dried crystals were slurried in water, the resulting slurry basified and then extracted with methylene chloride. The methylene chloride extract was treated with diatomaceous earth and activated charcoal and then filtered. The methylene chloride was evaporated and 27.4 g of the free imidazoline obtained, m.p. 116°-118° C. The free imidazoline was then put in solution in isopropyl alcohol and acidified with HCl in isopropyl alcohol. The mixture was then cooled and filtered which gave 27.4 g of 2-((4-chlorophenoxy)methyl)-2-imidazoline hydrochloride, m.p. 185°-186° C.

後処理

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe crystals that were obtained
  5. customwere dried in a vacuum oven
  6. extractionextracted with methylene chloride
  7. extractionThe methylene chloride extract
  8. additionwas treated with diatomaceous earth and activated charcoal
  9. filtrationfiltered
  10. customThe methylene chloride was evaporated

出典と根拠

ORDレコード
ord-df29524393e74970aa34b15ba66ebab5
出典データセット
uspto-grants-1982_08
特許番号
US04343809

関連ノート

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