Methoxyacetyl chloride → 2-Methoxymethyl-1-(tetrahydropyran-4-yl)-5-trifluoromethylbenzimidazole

HRID 74161

반응식

HRID 74161 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[CH3:19][O:20][CH2:21][C:22](Cl)=O>O1CCOCC1>[CH3:19][O:20][CH2:21][C:22]1[N:12]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[N:1]=1

참가 물질

4

반응물 2

HCID 96623Methoxyacetyl chlorideHCID 185097862-Amino-1-(tetrahydropyran-4-yl)amino-4-trifluoromethylbenzene

생성물 1

HCID 674980032-Methoxymethyl-1-(tetrahydropyran-4-yl)-5-trifluoromethylbenzimidazole수율 77.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

A 4-neck flask equipped with a reflux condenser was charged with 2-amino-1-(tetrahydropyran-4-yl)amino-4-trifluoromethylbenzene (see Synthesis Example 4) (0.62 g, 2.38 mmol) and anhydrous 1,4-dioxane (8.5 mL) and this was refluxed. Methoxyacetyl chloride (0.57 g, 5.25 mmol) in 1,4-dioxane solution (approx. 1.5 mL) was added dropwise to this over approximately 10 m. This was stirred under these conditions for 2 hours. This was allowed to cool, distilled water was added, and the solvent was distilled off under reduced pressure. This was successively extracted with t-butyl methyl ether, washed with brine, and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to yield the title compound (0.58 g, 77.4% yield) as a white powder.

후처리

  1. customA 4-neck flask equipped with a reflux condenser
  2. temperaturethis was refluxed
  3. temperatureto cool
  4. distillationdistilled water
  5. additionwas added
  6. distillationthe solvent was distilled off under reduced pressure
  7. extractionThis was successively extracted with t-butyl methyl ether
  8. washwashed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-58751571c5b4443d864158446583478d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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