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Thionyl Chloride → HCID 66654660, 화합물

HRID 517718
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HRID 517718 반응식
O[CH2:2][C:3]1[N:7]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[C:11]([NH2:13])=[O:12])[N:6]=[N:5][N:4]=1.S(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][CH2:2][C:3]1[N:7]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[C:11]([NH2:13])=[O:12])[N:6]=[N:5][N:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 666547173-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-(trifluoromethyl)benzamide

생성물 1

HCID 66654660HCID 66654660, 화합물수율 67.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a suspension of 3-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-5-(trifluoromethyl)benzamide (500 mg, 1.741 mmol) in toluene (5 mL) was added thionyl chloride (0.140 mL, 1.92 mmol) and the reaction heated to reflux for 4 hours. The reaction was allowed to cool and the solvent removed under vacuum. The residue was partitioned between DCM (20 mL) and water (10 mL). The organic layer collected via a hydrophobic frit and the solvent removed under vacuum. The residue was purified by silica chromatography (Biotage SP4, eluting 10% EtOAc in iso-hexane (5 column volumes) then a gradient from 10-100% EtOAc in iso-hexane (over 10 column volumes)) to yield the title compound as a pale yellow gum (360 mg).

후처리

  1. temperaturethe reaction heated
  2. temperatureto reflux for 4 hours
  3. temperatureto cool
  4. customthe solvent removed under vacuum
  5. customThe residue was partitioned between DCM (20 mL) and water (10 mL)
  6. customThe organic layer collected via a hydrophobic frit
  7. customthe solvent removed under vacuum
  8. customThe residue was purified by silica chromatography (Biotage SP4
  9. washeluting 10% EtOAc in iso-hexane (5 column volumes)

출처 및 근거

ORD 기록
ord-1f723407aef34e0fb32174bcac07f368
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115132B2

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