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

HRID 236107
ノート
印刷プレビュー

反応式

HRID 236107 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7ff3854e125145098828b0ff4464811a
出典データセット
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04642348

反応ノート

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