Acetonitrile → HCID 638695、化合物

HRID 2109195ノート

反応式

HRID 2109195 の反応式
I.[CH3:2][NH:3][C:4](=[NH:7])[S:5][CH3:6].Br[C:9](=[CH:12][O:13]C(C)C)[CH:10]=[O:11].CC#N.C([O-])([O-])=O.[K+].[K+]>O>[CH3:2][N:3]1[C:9]([CH:10]=[O:11])=[CH:12][N:7]=[C:4]1[S:5][CH3:6].[CH3:2][N:3]1[CH:10]=[C:9]([CH:12]=[O:13])[N:7]=[C:4]1[S:5][CH3:6]

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 534166342-Bromo-3-isopropoxy-propenalHCID 178485204HCID 178485204、化合物

生成物 2

HCID 638695HCID 638695、化合物HCID 210972441H-Imidazole-4-carboxaldehyde, 1-methyl-2-(methylthio)- (9CI)

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
35 °C

実験手順

To a mixture of 2.65 g (11.4 mmol) of 1,2-dimethyl-isothiourea hydroiodide and 1.00 g (10.4 mmol) of 2-bromo-3-isopropoxy-propenal 8 mL of MeCN was added 1.58 g (11.4 mmol) of K2CO3 (Shilcrat, S. C. et al. J. Org. Chem., 1997, 62, 8449-8454). The mixture was stirred at 35° C. under N2 for 16 h, water (20 ml) was added, and the mixture was extracted with CH2Cl2 (200 mL). The extract was dried over MgSO4, filtered, concentrated, and chromatographed (0 to 100% EtOAc in hexanes) to provide 1.09 g of 3-methyl-2-methylsulfanyl-3H-imidazole-4-carbaldehyde and 284 mg of 1-methyl-2-methylsulfanyl-1H-imidazole-4-carbaldehyde.

後処理

  1. extractionthe mixture was extracted with CH2Cl2 (200 mL)
  2. dry with materialThe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (0 to 100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-385672a13981422c86c6ba3e8f8d7fbb
出典データセット
uspto-grants-2009_04
特許番号
US07514458B2

反応ノート

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