Methane, dichloromethoxy- → HCID 178418754, 화합물

HRID 10729

반응식

HRID 10729 반응식
[CH:1]1([C:4]2[NH:5][CH:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=3[O:17][CH3:18])[N:8]=2)[CH2:3][CH2:2]1.[CH3:19][O:20]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl>[CH:1]1([C:4]2[NH:5][CH:6]=[C:7]([C:9]3[C:10]([O:17][CH3:18])=[CH:11][C:12]([O:15][CH3:16])=[C:13]([CH:14]=3)[CH:19]=[O:20])[N:8]=2)[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 21004Methane, dichloromethoxy-HCID 178418803HCID 178418803, 화합물

생성물 1

HCID 178418754HCID 178418754, 화합물

시약·촉매·용매 1

HCID 24193Titanium Tetrachloride촉매

실험 절차

Ex-105B: To a solution of 2-cyclopropyl-4-(2,4-dimethoxy-phenyl)-1H-imidazole (0.51 g, 2.09 mmol) was added dichloromethyl methyl ether (0.28 mL, 3.13 mmol) followed by addition of titanium tetrachloride (1.0M in dichloromethane, 8.4 mL, 8.4 mmol) dropwise at 0° C. The solution was allowed to warm up to ambient temperature and stir for 4.5 hours. The reaction mixture was then poured into ice. The aqueous layer was adjusted to pH 12 and extracted with dichloromethane. The combined solution of dichloromethane was washed with saturated solution of sodium bicarbonate, brine, dried over sodium sulfate and concentrated to afford 5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde which was used without further purification. 1H NMR (DMSO-d6) δ 13.95 (bs, 1H), 10.22 (s, 1H), 8.09 (s, 1H), 7.70 (s, 1H), 6.88 (s, 1H), 4.04 (s, 3H), 4.00 (s, 3H), 2.25 (m, 1H), 1.20 (m, 4H). MS m/z=245 ([M+H]+, 100%).

후처리

  1. additionThe reaction mixture was then poured into ice
  2. extractionextracted with dichloromethane
  3. washThe combined solution of dichloromethane was washed with saturated solution of sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fcfe69e46057466bbea048d283df22b7
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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