Water → 1-[3-(Ethoxycarbonyl)propyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383963

반응식

HRID 1383963 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]2[NH:11][C:12]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1.[CH2:22]([O:24][C:25]([CH2:27][CH2:28][CH2:29]Br)=[O:26])[CH3:23].O>CN(C)C=O>[CH2:22]([O:24][C:25]([CH2:27][CH2:28][CH2:29][N:14]1[C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:12]=2[N:11]=[C:10]1[CH2:9][O:8][C:7]1[CH:20]=[CH:21][C:4]([Cl:3])=[CH:5][CH:6]=1)=[O:26])[CH3:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 178423973HCID 178423973, 화합물

생성물 1

HCID 211886461-[3-(Ethoxycarbonyl)propyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole수율 111.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A sodium hydride solution (60% in oil, 325 mg, 8.1 mmol) was washed with hexanes (2×50 ml) and then diluted with N,N-dimethylformamide (100 ml). At room temperature, under a nitrogen atmosphere, 2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (2.0 g, 7.3 mmol) was then added in one portion. The resulting mixture was then stirred at room temperature for thirty minutes, and then 3-(ethoxycarbonyl)propyl bromide (1.58 g, 8.1 mmol) in N,N-dimethylformamide (10 ml) was added dropwise. Upon completion of this addition, the reaction mixture was stirred for about six hours at a temperature of 70-80° C. The reaction mixture was then cooled to room temperature, poured into water (500 ml), and then extracted with ethyl acetate (500 ml). The organic fraction was washed once with water (500 ml) and then dried over potassium carbonate. The solvents were removed in vacuo, yielding 3.16 grams of a semi-solid material. The crude material was firther purified by flash silica gel chromatography, eluting with a gradient solvent of methylene chloride to 1:1 methylene chloride:ethyl acetate. The fractions containing the desired title product were combined and concentrated in vacuo to yield 2.21 grams (78%) of a viscous yellow oil.

후처리

  1. additionUpon completion of this addition
  2. stirringthe reaction mixture was stirred for about six hours at a temperature of 70-80° C
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. extractionextracted with ethyl acetate (500 ml)
  5. washThe organic fraction was washed once with water (500 ml)
  6. dry with materialdried over potassium carbonate
  7. customThe solvents were removed in vacuo

출처 및 근거

ORD 기록
ord-1846c0a69387486a977c49402dc84168
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255494B1

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