Diisopropylethylamine → 5-(3-Chloro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-[1,2,4]oxadiazole

HRID 732082Notes

Reaction equation

HRID 732082 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([CH3:11])[C:9](=O)[CH2:8][N:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1.CCN(C(C)C)C(C)C.Cl[CH2:45][C:46]1[N:50]=[C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([Cl:57])[CH:52]=2)[O:48][N:47]=1>O1CCOCC1.C(OCC)(=O)C>[Cl:57][C:53]1[CH:52]=[C:51]([C:49]2[O:48][N:47]=[C:46]([CH2:45][S:22][C:9]3[N:10]([CH3:11])[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[N:7][CH:8]=3)[N:50]=2)[CH:56]=[CH:55][CH:54]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 87949Lawesson's reagentHCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazoleHCID 670708452-Furan-2-yl-3-methyl-3,5-dihydro-imidazol-4-one

Product 1

HCID 670709295-(3-Chloro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-[1,2,4]oxadiazoleYield 11.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Furan-2-yl-3-methyl-3,5-dihydro-imidazol-4-one (described in Takeuchi, H., Hagiwara, S., Eguchi, S., Tetrahedron (1989) 6375-6386) (50 mg, 0.30 mmol) was dissolved in dioxane (3 ml) and Lawesson reagent (136 mg, 0.34 mmol) was added. The reaction mixture was heated to reflux over night and then allowed to room temperature at which time DIPEA (212 ml, 1.22 mmol) and 3-chloromethyl-5-(3-chloro-phenyl)-[1,2,4]oxadiazole (140 mg, 0.61 mmol) was added. The resulting mixture was heated to reflux for 5 h and then kept at room temperature over night. Ethyl acetate was added and the reaction mixture was washed with water followed by brine. The organic phase was dried over MgSO4 and evaporated. The title compound (13 mg, 11%) was obtained by flash chromatography using 1% methanol in chloroform. 1H NMR (CD3OD) d (ppm): 7.96 (m, 1 H), 7.90 (m, 1H), 7.60 (dd, 1H), 7.57 (ddd, 1H), 7.46 (t, 1H), 7.09 (s, 1H), 6.86 (dd, 1H), 6.52 (dd, 1H), 3.95 (s, 2H), 3.74 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux over night
  3. additionwas added
  4. temperatureThe resulting mixture was heated
  5. temperatureto reflux for 5 h
  6. waitkept at room temperature over night
  7. washthe reaction mixture was washed with water
  8. dry with materialThe organic phase was dried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-09adfff7319d4eb6b352a4ce549e69f7
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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