5-Nitrofurfural → HCID 178519733, 화합물

HRID 1696680

반응식

HRID 1696680 반응식
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[N+]([C:21]1[O:25][C:24]([CH:26]=[O:27])=[CH:23][CH:22]=1)([O-])=O>O1CCCC1>[F:14][C:12]([F:15])([F:13])[O:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][C:21]3[O:25][C:24]([CH:26]=[O:27])=[CH:23][CH:22]=3)=[N:3][C:4]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178506355HCID 178506355, 화합물

생성물 1

HCID 178519733HCID 178519733, 화합물수율 62.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 2-mercapto-5-trifluoromethoxy-benzimidazole (1.26 g, 5.38 mmol) in tetrahydrofuran (10 ml) is added dropwise to a mixture of sodium hydride (60% dispersion in mineral oil, 0.344 g, 8.61 mmol) and tetrahydrofuran (5 ml) at 0° C. The mixture is stirred at room temperature for 2 hours. A solution of 5-nitro-2-furaldehyde (0.76 g, 5.38 mmol) in tetrahydrofuran (15 ml) is then added dropwise over a 15 minute period and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated under reduced pressure and the residue is dissolved in 10 ml of dichloromethane and filtered through a silica gel plug (40 ml). The silica gel plug is eluted with 800 ml of cylohexane/ethyl acetate (7/3, v/v). The organic filtrates are combined and concentrated under reduced pressure to yield 1.1 g of 5-(5-trifluoromethoxy-1H-benzoimidazol-2-ylsulfanyl)-furan-2-carbaldehyde as an oil. Yield=62%. Analytical LC/MS (method B): retention time=3.77 min., m/z=329.0 (positive ion mode).

후처리

  1. stirringthe mixture is stirred for 16 hours at room temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in 10 ml of dichloromethane
  4. filtrationfiltered through a silica gel plug (40 ml)
  5. washThe silica gel plug is eluted with 800 ml of cylohexane/ethyl acetate (7/3
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-15a61c4e45b94032b954eb665463ae8f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163768B2

연결된 노트

불러오는 중…