Carbon Tetrachloride → HCID 67350127, compound

HRID 1672782Notes

Reaction equation

HRID 1672782 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([NH:7][NH:8][C:9](=[O:12])[CH2:10][CH3:11])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C>C(#N)C>[CH2:10]([C:9]1[O:12][C:5]([C:4]2[CH:13]=[CH:14][CH:15]=[C:2]([I:1])[CH:3]=2)=[N:7][N:8]=1)[CH3:11]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 67350108HCID 67350108, compound

Product 1

HCID 67350127HCID 67350127, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

3-Iodo-N′-propionylbenzohydrazide (382 mg, 1.20 mmol) obtained in Step 2 was dissolved in acetonitrile (21 mL), and the mixture was stirred at 60° C. for 2 hours after adding triphenylphosphine (629 mg, 2.40 mmol), carbon tetrachloride (0.46 mL, 4.80 mmol), and triethylamine (0.33 mL, 1.54 mmol). After concentrating the mixture under reduced pressure, the residue was purified by silica gel column chromatography to give 2-ethyl-5-(3-iodophenyl)-1,3,4-oxadiazole (331 mg, 92%).

Workup

  1. concentrationAfter concentrating the mixture under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b51fc34ace2940e4a44c934713735536
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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