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1,1'-Thiocarbonyldiimidazole → tert-Butyl 4-carbamothioylpiperazine-1-carboxylate

HRID 238661
ノート
印刷プレビュー

反応式

HRID 238661 の反応式
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=[S:2].[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>O1CCCC1>[NH2:3][C:1](=[S:2])[N:16]1[CH2:17][CH2:18][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:15]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 12093220tert-Butyl 4-carbamothioylpiperazine-1-carboxylate収率 56.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of thiocarbonyldiimidazole (2.1 g, 11.8 mmol) in tetrahydrofuran (30 mL) at room temperature, was added 1,1-dimethylethyl 1-piperazinecarboxylate (2 g, 10.75 mmol). The reaction mixture was stirred at room temperature for 2 h and then heated to 55° C. for additional 2 h. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure until approximately 20 mL of tetrahydrofuran remained. The residue was then treated with a 2 M solution of ammonia in methanol (10 mL) and stirred at room temperature for 24 h. The reaction mixture was concentrated under reduced pressure, and the residue was triturated with diethyl ether (25 mL) to give a white precipitate. The precipitate was filtered and dried to give 1.5 g of the title compound as a white solid.

後処理

  1. temperatureheated to 55° C. for additional 2 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure until approximately 20 mL of tetrahydrofuran
  4. additionThe residue was then treated with a 2 M solution of ammonia in methanol (10 mL)
  5. stirringstirred at room temperature for 24 h
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe residue was triturated with diethyl ether (25 mL)
  8. customto give a white precipitate
  9. filtrationThe precipitate was filtered
  10. customdried

出典と根拠

ORDレコード
ord-cda6c91cb0ba4bd4bdd248c7d4410322
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642634B2

反応ノート

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