Dimethylformamide dimethyl acetal → HCID 67519860, compound

HRID 1925208Notes

Reaction equation

HRID 1925208 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]2[N:14]([C:15]=1[C:16](=[O:18])[CH3:17])[CH:13]=[CH:12][O:11]2.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>C(OCC)(=O)C>[CH3:21][N:22]([CH3:24])[CH:23]=[CH:17][C:16]([C:15]1[N:14]2[C:10]([O:11][CH:12]=[CH:13]2)=[N:9][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[O:18]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 576729731-[6-(2-Chlorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone

Product 1

HCID 67519860HCID 67519860, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 50 ml round bottom flask is charged with the 1-[6-(2-chlorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone (952 mg, 3.65 mmol) and dimethylformamide dimethylacetal (22 ml). The mixture is refluxed for 5 hours and then cooled to room temperature. The mixture is diluted with ethyl acetate (150 ml) and washed three times with 100 ml each of a saturated sodium chloride solution. The organic phase is dried with magnesium sulfate, filtered and concentrated in vacuo, to give a brown oil. The product is purified by flash chromatography on silica gel (ethyl acetate), yielding 604 mg of a pale brown solid (52%). M.p.=187-189° C.; 300 MHz 1H NMR (CDCl3) δ: 8.07 (d, J=1.6 Hz, 1H), 7.62-7.35 (m, 6H), 4.78 (d, J=12.5 Hz), 1H), 3.04-3.01 (m, 3H), 2.4-2.32 (m, 3H). LCMS: 316[M+H]; calc. for C16H14ClN3O2: C, 60.76; H, 4.49; N, 13.28; found. C, 60.81; H, 4.39; N, 13.35.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. washwashed three times with 100 ml each of a saturated sodium chloride solution
  3. dry with materialThe organic phase is dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customThe product is purified by flash chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-3123a316caf14af49f6bf02f5eda86e0
Source dataset
uspto-grants-2012_05
Patent number
US08178672B2

Reaction notes

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