Benzoyl isothiocyanate → 4-{[(benzoylamino)carbonothioyl][(2-butyl-4-chloro-1H-imidazol-5-yl)methlyl]amino}-1H-imidazole-5-carboxamide

HRID 912662ノート

反応式

HRID 912662 の反応式
[CH2:1]([C:5]1[NH:6][C:7]([CH2:11][NH:12][C:13]2[N:14]=[CH:15][NH:16][C:17]=2[C:18]([NH2:20])=[O:19])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:21]([N:29]=[C:30]=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.CO>[C:21]([NH:29][C:30]([CH:11]([NH:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([NH2:20])=[O:19])[C:7]1[NH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][C:8]=1[Cl:10])=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 2

HCID 68284Benzoyl isothiocyanateHCID 674141614-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide

生成物 1

HCID 1317291954-{[(benzoylamino)carbonothioyl][(2-butyl-4-chloro-1H-imidazol-5-yl)methlyl]amino}-1H-imidazole-5-carboxamide収率 38%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

4-{[(2-Butyl-4-chloro-1H-imidazol-5-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.30 g, 1.01 mmol, obtained from Example 7(a)) was dissolved in CH2Cl2 (5 mL) and methanol (2 mL). Benzoylisothiocyanate (0.18 g, 1.11 mmol) was added and the mixture was stirred at r.t. for 4 h. The mixture was then concentrated in vacuo and dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.175 g (38%) of the title compound. MS (ESI) m/z 460 (M+1).

後処理

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol)

出典と根拠

ORDレコード
ord-1a9c1ad27aa14b9cb4ccd4b515516c50
出典データセット
uspto-grants-2011_09
特許番号
US08026244B2

反応ノート

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