Hydrochloric Acid → HCID 59978349, compound

HRID 1759912Notes

Reaction equation

HRID 1759912 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[C:2]#[C:3][CH3:4].Cl.[CH2:21]([O:23][NH2:24])[CH3:22].Cl>N1C=CC=CC=1>[CH2:21]([O:23][N:24]=[C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]1[CH:7]=[C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])[N:11]=[CH:10][N:9]=1)[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 76850O-ethylhydroxylamine hydrochlorideHCID 22599721HCID 22599721, compound

Product 1

HCID 59978349HCID 59978349, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 3 ml of pyridine were added 0.3 g of 6-(2-butynyloxy)-4-benzoylpyrimidine and 0.17 g of O-ethylhydroxylamine hydrochloride, followed by stirring at room temperature for 3 hours. The reaction mixture was then poured into 10% hydrochloric acid and extracted three times with ethyl acetate. The organic layers were combined and washed with a saturated aqueous sodium chloride solution, and the combined organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give two isomers of (6-(2-butynyloxy)-4-pyrimidyl)phenylketone O-ethyloxime (referred to as isomers A and B).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-233f02f9e18c4da49513cb7e714e3f4d
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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