Acetonitrile → HCID 638695, 화합물

HRID 1350690노트

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HRID 1350690 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-aa359d021bd04eb1a0f5790763575632
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214802B2

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