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Thionyl Chloride → HCID 66654350, 화합물

HRID 517740
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HRID 517740 반응식
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:11]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][C:21]([F:24])([F:23])[F:22])[CH:13]=2)[N:10]=[N:9][N:8]=1>C1(C)C=CC=CC=1>[Cl:3][CH2:6][C:7]1[N:11]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][C:21]([F:24])([F:23])[F:22])[CH:13]=2)[N:10]=[N:9][N:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 66654249HCID 66654249, 화합물2회

생성물 1

HCID 66654350HCID 66654350, 화합물수율 76.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Thionyl chloride (2.21 g, 18.6 mmol) was added to a stirred solution of 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-2-[(trifluoromethyl)oxy]benzonitrile (Intermediate 54, 3.50 g, 12.3 mmol) in toluene (50 mL) at room temperature, and the reaction mixture was heated to reflux for 4 h. The reaction mixture was concentrated under vacuum. The residue was diluted with DCM and washed with ice-cooled water, saturated aq NaHCO3 and brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. This was purified by column chromatography (60-120 mesh silica gel), eluting with 20% EtOAc/pet.ether to give the title compound as an off-white powder (2.85 g).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionThe residue was diluted with DCM
  5. washwashed with ice-
  6. temperaturecooled water, saturated aq NaHCO3 and brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto give the crude product
  10. customThis was purified by column chromatography (60-120 mesh silica gel)
  11. washeluting with 20% EtOAc/pet

출처 및 근거

ORD 기록
ord-038c62c72de24593ba5bfee57feec210
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115132B2

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