Water → 2-Ethoxy-5-methyl-1-[3-(trifluoromethyl)phenyl]-1H-imidazole

HRID 1480018노트

반응식

HRID 1480018 반응식
F[B-](F)(F)F.C([O+:8]([CH2:11][CH3:12])[CH2:9]C)C.[CH3:13][C:14]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)C(=O)[NH:16][CH:15]=1.O.[OH-].[Na+]>C(Cl)Cl>[CH2:11]([O:8][C:9]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[C:14]([CH3:13])=[CH:15][N:16]=1)[CH3:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2723982Triethyloxonium tetrafluoroborateHCID 814460105-Methyl-1-[3-(trifluoromethyl)phenyl]-1,3-dihydro-2H-imidazol-2-one

생성물 1

HCID 1213937382-Ethoxy-5-methyl-1-[3-(trifluoromethyl)phenyl]-1H-imidazole수율 79.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of triethyloxonium tetrafluoroborate (9.0 g, 47 mmol) in DCM (62 mL) was added to a stirred solution of 5-methyl-1-[3-(trifluoromethyl)phenyl]-1,3-dihydro-2H-imidazol-2-one (9.0 g, 37 mmol) in DCM (124 mL) under a nitrogen atmosphere. The solution was stirred at RT for 2.5 h then treated with water (50 mL) then 1 M sodium hydroxide (50 mL). The phases were partitioned. The aqueous phase was washed with DCM (2×50 mL). The combined organic phase was dried (sodium sulfate). The solution of the crude product was filtered through 2×50 g flash SCX 2 cartridges. Each cartridge was rinsed with 10% methanol in DCM (100 mL) then the product fraction was eluted with 2M methanolic ammonia solution (100 mL). The fractions recovered with methanolic ammonia were combined and concentrated in vacuo to afford the title compound (7.92 g) as a brown solid.

후처리

  1. customThe phases were partitioned
  2. washThe aqueous phase was washed with DCM (2×50 mL)
  3. dry with materialThe combined organic phase was dried (sodium sulfate)
  4. filtrationThe solution of the crude product was filtered through 2×50 g flash SCX 2 cartridges
  5. washEach cartridge was rinsed with 10% methanol in DCM (100 mL)
  6. washthe product fraction was eluted with 2M methanolic ammonia solution (100 mL)
  7. customThe fractions recovered with methanolic ammonia
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-40d6001110db48b39121332135f4da66
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409870B2

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