Phosphorus oxychloride → 2-Chloro-5-methyl-1,3-benzoxazole

HRID 563719

반응식

HRID 563719 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](S)=[N:7][C:6]=2[CH:11]=1.P(Cl)(Cl)([Cl:14])=O.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Cl:14][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:6]=2[N:7]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178423563HCID 178423563, 화합물

생성물 1

HCID 99896072-Chloro-5-methyl-1,3-benzoxazole

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Methyl-benzooxazole-2-thiol (5.0 g, 30.2 mmol), phosphorus oxychloride (25.0 mL, 269.4 mmol), and phosphorus pentachloride (7.56 g, 36.3 mmol) were combined in CH2Cl2 (30 mL), and the reaction was stirred at room temperature overnight. The mixture was concentrated several times from fresh CH2Cl2 to remove traces of phosphorus oxychloride, and the residue was treated with saturated aqueous Na2CO3 to adjust to pH 8. The aqueous layer was extracted twice with CH2Cl2, and the combined organic layers were washed with H2O and brine, and then dried over Na2SO4, decanted, and concentrated. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

후처리

  1. concentrationThe mixture was concentrated several times from fresh CH2Cl2
  2. customto remove traces of phosphorus oxychloride
  3. additionthe residue was treated with saturated aqueous Na2CO3
  4. extractionThe aqueous layer was extracted twice with CH2Cl2
  5. washthe combined organic layers were washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated
  9. customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-35365d21e69b463cb7e461ec1face7ed
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067445B2

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