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

HRID 563719ノート

反応式

HRID 563719 の反応式
[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

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178423563HCID 178423563、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-35365d21e69b463cb7e461ec1face7ed
出典データセット
uspto-grants-2011_11
特許番号
US08067445B2

反応ノート

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