Phosgene → HCID 90411618, compound

HRID 2170835Notes

Reaction equation

HRID 2170835 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[O:11])=[CH:4][CH:3]=1.[O:17]1CCC[CH2:18]1.C(Cl)(Cl)=O.C(OCC)(=O)C>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:9]=[C:10]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:18]2=[O:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 2812134HCID 2812134, compound

Product 1

HCID 90411618HCID 90411618, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N′-(4-fluorophenyl)thiophene-2-carbohydrazide (575 mg, 2.43 mmol) was dissolved in dichloromethane (14 mL) and tetrahydrofuran (10 mL) in a glass flask. The flask was cooled in ice. Phosgene (20% in toluene, 3.42 mL, 6.49 mmol, 2.67 eq.) was added, and the solution was stirred overnight under a nitrogen atmosphere, allowing it to warm to room temperature. Ethyl acetate (40 mL) was added, and the solution was then washed with water (2×25 mL) and brine (25 mL). The solution was dried over magnesium sulfate, filtered and concentrated in vacuo to give 0.59 grams of crude product as a light brown solid. Purification using ISCO flash chromatography (silica, gradient heptanes/ethyl acetate) gave 3-(4-fluorophenyl)-5-(thiophen-2-yl)-1,3,4-oxadiazol-2(3H)-one (210 mg, 0.800 mmol, yield 33.0%) as an off-white solid with an HPLC purity of 99.7%. LC-MS [M+H] 263.02 (C12H7FN2O2S+H, expected 263.02). The 1H-NMR spectrum was in accordance with the chemical structure.

Workup

  1. temperatureThe flask was cooled in ice
  2. washthe solution was then washed with water (2×25 mL) and brine (25 mL)
  3. dry with materialThe solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give 0.59 grams of crude product as a light brown solid
  7. customPurification

Sources & evidence

ORD record
ord-796b49372129477abc2202f19c07733c
Source dataset
uspto-grants-2015_06
Patent number
US09051309B2

Reaction notes

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