Carbon Tetrachloride → 5-(2-bromophenyl)-N-phenyl-1,3,4-oxadiazol-2-amine

HRID 558170Notes

Reaction equation

HRID 558170 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>C(Cl)Cl.C(OCC)(=O)C.O1CCCC1>[Br:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]1[O:9][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:7][N:6]=1

Participants

8

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 9134981-(2-Bromobenzoyl)-4-phenylsemicarbazide

Product 1

HCID 591525395-(2-bromophenyl)-N-phenyl-1,3,4-oxadiazol-2-amineYield 83.9%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-bromobenzoyl)-4-phenylsemicarbazide (330 mg, 0.98 mmol; Reference Compound 5-(1)), triphenylphosphine (390 mg, 1.5 mmol) and triethylamine (0.20 mL, 9.7 mmol) in methylene chloride (30 mL) were added carbon tetrachloride (2.5 mL, 1.4 mmol) and tetrahydrofuran (5 mL) under ice-cooling. The mixture was refluxed for 2 hours and then cooled to room temperature. Ethyl acetate (20 mL) was added thereto and the ethyl acetate solution was washed with a saturated brine solution (20 mL) twice, dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to dryness. The residue was purified with a silica gel column chromatography (hexane/ethyl acetate) to give 260 mg (82%) of the titled compound as a colorless solid.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 2 hours
  3. washthe ethyl acetate solution was washed with a saturated brine solution (20 mL) twice
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure to dryness
  6. customThe residue was purified with a silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2ea1cbeb4d1d45ecb19e35778f15b2ca
Source dataset
uspto-grants-2011_11
Patent number
US08063034B2

Reaction notes

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