Dimethylformamide dimethyl acetal → 3-(Dimethylamino)-1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]prop-2-en-1-one

HRID 1925213Notes

Reaction equation

HRID 1925213 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16](=[O:18])[CH3:17])[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>>[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:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:18]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 167264821-[6-(4-Fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone

Product 1

HCID 675198943-(Dimethylamino)-1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]prop-2-en-1-oneYield 87%

Procedure

A 2 L 3-neck round bottom flask is charged with 1-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]ethanone (215 g, 0.88 mol) and dimethylformamide dimethylacetal (1.1 L). The mixture is refluxed for 5 hours and then cooled to room temperature. Solvent is removed under vacuum, and the resulting solid is filtered and washed with MTBE (methyl tert-butyl ether) to give the desired product (229.0 g) in 87% yield as light yellow solid. M.p.=187-189° C.; 300 MHz 1H NMR (CDCl3) δ 8.03 (s, 1H), 7.72-7.64 (m, 3H), 7.46 (s, 1H), 7.13-7.10 (m, 2H), 5.19 (d, J=12.5 Hz, 1H), 3.07 (bs, 3H), 2.55 (bs, 3H). LCMS: 300 [M+H]. Calc. for C16H14FN3O2: C, 64.21; H, 4.71; N, 14.04; found. C, 64.22; H, 4.31; N, 14.10.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. customSolvent is removed under vacuum
  3. filtrationthe resulting solid is filtered
  4. washwashed with MTBE (methyl tert-butyl ether)

Sources & evidence

ORD record
ord-1579147e9c1b4a18a596a7e8ceb953d4
Source dataset
uspto-grants-2012_05
Patent number
US08178672B2

Reaction notes

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