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

HRID 66384Notes

Reaction equation

HRID 66384 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c271a9dab13444438170bbd2b80084db
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Reaction notes

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