Acetonitrile → HCID 638695, 화합물

HRID 2109195노트

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HRID 2109195 반응식
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]

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 534166342-Bromo-3-isopropoxy-propenalHCID 178485204HCID 178485204, 화합물

생성물 2

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

시약·촉매·용매 1

HCID 962Water용매

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온도
35 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-385672a13981422c86c6ba3e8f8d7fbb
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514458B2

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