2-Furancarbonyl chloride → HCID 46850915, compound

HRID 908096Notes

Reaction equation

HRID 908096 reaction equation
[OH:1][NH:2][C:3](=[NH:12])[O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.CCN(C(C)C)C(C)C.[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](Cl)=O>O1CCOCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:3]2[N:12]=[C:27]([C:23]3[O:22][CH:26]=[CH:25][CH:24]=3)[O:1][N:2]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 178513443HCID 178513443, compound

Product 1

HCID 46850915HCID 46850915, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the mixture of 4-chlorophenyl hydroxycarbamimidate (0.5 mmol. 1 eq) and DIEA (1.25 mmol, 2.5 eq) in dioxane was added dropwise furan-2-carbonyl chloride (0.53 mmol, 1.05 eq) at 0-5° C. The mixture was allowed to warm to room temperature and then stirred for 0.5-1 h or until complete as determined by LC-MS analysis of the reaction mixture. The cyclodehydration reaction was run at reflux (115-120° C.) overnight. The mixture was cooled down and solvent was removed in vacuo. The resulting residue was purified by HPLC purification to provide desired 3-(4-Chloro-phenoxy)-5-furan-2-yl-[1,2,4]oxadiazole in a yield of 50% and purity of 99.9%. LC-MS [M+H] 263.3 (C12H7ClN2O3+H, requires 263.65). 1H NMR (DMSO-d6) δ 8.17 (d, 1H, J=1.75), 7.63 (d, 1H, J=3.5), 7.55 (d, 2H, J=8.8), 7.46 (d, 2H, J=8.8), 6.87 (m, 1H).

Workup

  1. customThe cyclodehydration reaction
  2. temperatureat reflux (115-120° C.) overnight
  3. temperatureThe mixture was cooled down
  4. customsolvent was removed in vacuo
  5. customThe resulting residue was purified by HPLC purification

Sources & evidence

ORD record
ord-e63aae88c04a496e827c7ccd0fd0d157
Source dataset
uspto-grants-2011_09
Patent number
US08017555B2

Reaction notes

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