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Methyl chloroformate → methyl N-[4-[4-(6-chloronaphthalen-2-yl)sulfonylpiperazine-1-carbonyl]benzenecarboximidoyl]carbamate

HRID 278605
ノート
印刷プレビュー

反応式

HRID 278605 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.C(N(CC)CC)C.Cl.[C:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)(=[NH:32])[NH2:31].Cl[C:43]([O:45][CH3:46])=[O:44]>ClCCl.CN(C=O)C>[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH2:18][N:19]([C:37](=[O:38])[C:36]3[CH:40]=[CH:41][C:33]([C:30](=[NH:32])[NH:31][C:43]([O:45][CH3:46])=[O:44])=[CH:34][CH:35]=3)[CH2:20][CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 226280844-Amidinobenzoylchloride hydrochlorideHCID 227097661-(6-Chloronaphth-2-ylsulphonyl)piperazine hydrochloride

生成物 1

HCID 145840733methyl N-[4-[4-(6-chloronaphthalen-2-yl)sulfonylpiperazine-1-carbonyl]benzenecarboximidoyl]carbamate収率 19.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride (143 mg) and triethylamine (208 mg) in dichloromethane (10 ml) was added 4-amidinobenzoylchloride hydrochloride (108 mg), and the solution was stirred at room temperature for 1 hour, to which were added DMF (10 ml) and methyl chloroformate (200 mg). The solution was stirred at 50° C. for 30 minutes and the reaction solution was concentrated . The residue was dissolved in ethyl acetate, washed with water and sodium chloride solution, dried and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate/methanol=40:1) to give colorless crystals of the title compound (41 mg).

後処理

  1. stirringThe solution was stirred at 50° C. for 30 minutes
  2. concentrationthe reaction solution was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel column chromatography (ethyl acetate/methanol=40:1)

出典と根拠

ORDレコード
ord-534365849e7048628c5e463a043d2464
出典データセット
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06359134B1

反応ノート

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