Water → 4-Chloro-2-(3-thienylmethyloxy)-6-(meta-trifluoromethylphenoxy)pyridine

HRID 55122노트

반응식

HRID 55122 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([O:22][CH2:23][C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[N:16]=1.O>CN(C)C(=O)C>[Cl:21][C:19]1[CH:20]=[C:15]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:16]=[C:17]([O:22][CH2:23][C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[CH:18]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 199573902,4-Dichloro-6-(3-thienylmethyloxy)pyridine

생성물 1

HCID 199574124-Chloro-2-(3-thienylmethyloxy)-6-(meta-trifluoromethylphenoxy)pyridine

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

To a solution of meta-trifluoromethylphenol (0.28 g, 0.0018×1.0 mol) in 10 ml of dry N,N-dimethylacetamide, sodium hydride (0.077 g, (ca.60% in mineral oil), 0.0018×1.1 mol) was added. After the bubbling ceased, a solution of 2,4-dichloro-6-(3-thienylmethyloxy)pyridine (0.46 g, 0.0018 mol) in 10 ml of dry N,N-dimethylacetamide was added dropwise and the resultant solution was stirred for about 7 hours at the temperature of 160° to 170° C. After allowed to cool, water was added to the reaction solution, then the mixture was partitioned by using ethyl acetate. The obtained organic layer was washed with aqueous saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off, then the residue was purified successively on silica gel column chromatography and on reversed phase column chromatography (Lobar column, Lichroprep RP-18, 40-63 μm, elution solvent: CH3CN/H2O=7/3(v/v)), whereby the end product was obtained.

후처리

  1. temperatureto cool
  2. customthe mixture was partitioned
  3. washThe obtained organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified successively on silica gel column chromatography and on reversed phase column chromatography (Lobar column, Lichroprep RP-18, 40-63 μm, elution solvent: CH3CN/H2O=7/3(v/v)), whereby the end product
  7. customwas obtained

출처 및 근거

ORD 기록
ord-52ac8f43bae54bb7b0d1b1fd35f86ba7
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624942

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