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1,1'-Carbonyldiimidazole → 3-[(4-Chlorophenyl)thio]-N-[2-(dimethylamino)ethyl]-1-pyrrolidinecarboxamid

HRID 236107
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HRID 236107 반응식
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[CH3:13]NN(CC)NC.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][CH:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:23][CH:22]=1>O1CCCC1>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([S:27][CH:28]2[CH2:32][CH2:31][N:30]([C:1]([NH:8][CH2:12][CH2:11][N:10]([CH3:9])[CH3:13])=[O:2])[CH2:29]2)=[CH:25][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 136079743-[(4-Chlorophenyl)sulfanyl]pyrrolidineHCID 57041336N,N-Dimethylaminoethylamine

생성물 1

HCID 136080063-[(4-Chlorophenyl)thio]-N-[2-(dimethylamino)ethyl]-1-pyrrolidinecarboxamid수율 69.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 5.20 g (0.032 mole) of 1,1'-carbonyldiimidazole and 2.73 g (0.031 mole) of N,N-dimethylaminoethylamine in 200 ml of tetrahydrofuran was stirred at room temperature for 50 min. A solution of 5.63 g (0.0264 mole) of 3-[(4-chlorophenyl)thio]pyrrolidine (free base) in tetrahydrofuran was added and the solution was refluxed for about 66 hr. The solvent was removed in vacuo and the resulting oil was dissolved in methylene chloride. The methylene chloride solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo and the resulting solid was recrystallized from methylene chloride-diethyl ether-hexane to give 6.03 g (69.7%) of white crystals, m.p. 97°-98.5° C.

후처리

  1. temperaturethe solution was refluxed for about 66 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting oil was dissolved in methylene chloride
  4. extractionThe methylene chloride solution was extracted with several portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe resulting solid was recrystallized from methylene chloride-diethyl ether-hexane

출처 및 근거

ORD 기록
ord-7ff3854e125145098828b0ff4464811a
출처 데이터셋
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04642348

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