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Phosphorus oxychloride → Methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate

HRID 1698591
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HRID 1698591 반응식
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=O)[NH:14][C:10]=2[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][C:13]1[N:12]([CH3:16])[C:11]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[C:10]=2[N:14]=1
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참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 67271829methyl 7-(1-ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

생성물 1

HCID 67273217Methyl 2-chloro-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate수율 85%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

A mixture of methyl 7-(1-ethylpropyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (1.30 g, 4.70 mmol) and phosphoryl chloride (10 ml) was heated at 100° C. for 3 h. The mixture was diluted with toluene and concentrated in vacuo to remove excess reagent. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on column silica gel with a 10% ethyl acetate/n-hexane to give 1.18 g (4.00 mmol, 85%) of the title compound as a colorless oil.

후처리

  1. concentrationconcentrated in vacuo
  2. customto remove excess reagent
  3. additionThe residue was diluted with aqueous saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on column silica gel with a 10% ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-703d12d38d9b4302aa5220d221c67258
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163935B2

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