Thionyl Chloride → 5-Chloromethyl-2-(5-methyl-2-phenyl-4-thiazolylmethoxy)pyridine

HRID 1295238노트

반응식

HRID 1295238 반응식
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=1.S(Cl)([Cl:25])=O>>[Cl:25][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:6][C:2]=2[CH3:1])=[N:20][CH:19]=1

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 229306846-(5-Methyl-2-phenyl-4-thiazolylmethoxy)-3-pyridylmethanol

생성물 1

HCID 229307085-Chloromethyl-2-(5-methyl-2-phenyl-4-thiazolylmethoxy)pyridine수율 92%

실험 절차

A mixture of 6-(5-methyl-2-phenyl-4-thiazolylmethoxy)-3-pyridylmethanol (1.56 g) and thionyl chloride (10 ml) was stirred at room temperature for 1 hr. The mixture was concentrated under reduced pressure and ice water was added to the residue. The mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and 5-chloromethyl-2-(5-methyl-2-phenyl-4-thiazolylmethoxy)pyridine (1.53 g, yield 92%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 78–79° C.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure and ice water
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2b8760ba44554eb1ad83627da63e6b6d
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241785B2

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