Dicyclohexylcarbodiimide → HCID 178502027、化合物

HRID 2367159ノート

反応式

HRID 2367159 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:21][O:22][C:23]([N:25]=[C:26]=S)=[O:24].C1CCC(N=C=NC2CCCCC2)CC1>C(#N)C.C1C=CC=CC=1>[CH3:21][O:22][C:23]([NH:25][C:26]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]([C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]([O:15][CH3:16])=[O:14])=[O:10])=[CH:3][C:2]=2[N:1]=1)=[O:24]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 552246Methoxycarbonyl isothiocyanateHCID 67044285Methyl 2-[(3,4-diaminophenyl)carbonyl]benzoate

生成物 1

HCID 178502027HCID 178502027、化合物収率 71%

試薬・触媒・溶媒 1

HCID 21919336Acetonitrile benzene溶媒

実験手順

To a solution of methyl 2-[(3,4-diaminophenyl)carbonyl]benzoate (134 mg, 0.50 mmol) in a mixture of acetonitrile-benzene (1:1, 5 mL) methyl isothiocyanatidocarbonate (70 mg, 0.60 mmol) was added followed by the addition of DCC (153 mg, 0.75 mmol) and the reaction mixture was heated to reflux for 18 h. After cooling to room temperature the reaction mixture was concentrated. The residue was triturated with diethyl ether (2×, 10 mL) and the pale orange solid was collected by filtration to give methyl 2-[(2-{[(methoxy)carbonyl]amino}-1H-benzimidazol-5-yl)carbonyl]benzoate (125 mg, 71%). MS (EI) for C18H15N3O5: 354 (M+H).

後処理

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 18 h
  4. concentrationwas concentrated
  5. customThe residue was triturated with diethyl ether (2×, 10 mL)
  6. filtrationthe pale orange solid was collected by filtration

出典と根拠

ORDレコード
ord-178054e1d32644feb4368bb5ec0b607d
出典データセット
uspto-grants-2014_04
特許番号
US08697737B2

反応ノート

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