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

HRID 66729

반응식

HRID 66729 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
178 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-df29524393e74970aa34b15ba66ebab5
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04343809

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