Triethylamine → Ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate

HRID 486983

반응식

HRID 486983 반응식
[CH3:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([Cl:10])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.Cl[C:19]([C:21]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:23][CH2:22]1)=[O:20]>O1CCCC1.CCOCC>[CH3:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([Cl:10])=[CH:5][C:3]=1[NH:4][C:19]([C:21]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:23][CH2:22]1)=[O:20]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 3437964,5-Dichloro-2-methylanilineHCID 14233946Ethyl 1-chlorocarbonylcyclopropanecarboxylate

생성물 1

HCID 19096823Ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

Into a nitrogen-purged round bottom flask was charged 5.53 grams (0.03 mole) of 2-methyl-4,5-dichloroaniline, 3.18 grams (0.03 mole) of triethylamine and 190 milliliters of tetrahydrofuran solvent. With vigorous stirring, a 5.55 gram (0.03 mole) portion of ethyl 1-chlorocarbonylcyclopropanecarboxylate prepared in Example XVIII was added in one portion, after which the mixture was stirred at ambient temperature for a six-hour period. A precipitate of triethylamine hydrochloride was then filtered off and the filtrate vacuum stripped to give a light yellow solid. The solid was taken up in ether and the solution water-washed, dried over magnesium sulfate, and solvent evaporated to give a yellow powder. Recrystallization from ethyl acetate-hexane gave 4.51 grams (0.01 mole) of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate having a melting point of 105° C.-107° C. Elemental analysis of the product indicated the following:

후처리

  1. customInto a nitrogen-purged round bottom flask
  2. filtrationA precipitate of triethylamine hydrochloride was then filtered off
  3. customto give a light yellow solid
  4. washthe solution water-washed
  5. dry with materialdried over magnesium sulfate, and solvent
  6. customevaporated
  7. customto give a yellow powder
  8. customRecrystallization from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-80b7e30efce7439ab9309941796df14b
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292937

연결된 노트

불러오는 중…