Dimethylformamide → 2-[3-(2-Dimethylaminoethoxy)phenyl]oxazolo[4,5-b]pyridine

HRID 259572노트

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HRID 259572 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=1.CN(C)C=O.C[O-].[Na+].Cl.[CH3:26][N:27]([CH2:29][CH2:30]Cl)[CH3:28]>CCOCC>[CH3:26][N:27]([CH3:28])[CH2:29][CH2:30][O:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 16127331HCID 16127331, 화합물

생성물 1

HCID 227547922-[3-(2-Dimethylaminoethoxy)phenyl]oxazolo[4,5-b]pyridine

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 1.1 g. (0.005 mole) of 2-(3-hydroxyphenyl)oxazolo[4,5-b]pyridine in 15 ml. dried dimethylformamide is added 0.6 g. (0.011 mole) of sodium methoxide in portions over about 10 min. To the reddish-orange solution cooled in an ice-bath is added 0.72 g. (0.005 mole) of N,N-dimethyl-2-chloroethylamine hydrochloride in portions over 15 minutes. The resultant mixture is then stirred 10 minutes, set in an oil-bath at 75° C., and kept at 75°-90° C. (bath) for 20 hours. After cooling to room temperature, 15 ml. of dried ether is added with stirring, and the resultant mixture is filtered. The filtrate is then stripped of solvent, and the residue distributed between methylene chloride and water. The organic layer is dried over sodium sulfate, filtered, and concentrated in vacuo to yield 2-[3-(2-dimethylaminoethoxy)phenyl]oxazolo[4,5-b]pyridine.

후처리

  1. temperatureTo the reddish-orange solution cooled in an ice-bath
  2. additionis added 0.72 g
  3. customset in an oil-bath at 75° C.
  4. customkept at 75°-90° C.
  5. customfor 20 hours
  6. filtrationthe resultant mixture is filtered
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8b0c362926684b0488378dc9fddc53fc
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04038396

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