Carbon Tetrachloride → HCID 67348658, compound

HRID 1672783Notes

Reaction equation

HRID 1672783 reaction equation
[CH:1]1([C:4]([NH:6][NH:7][C:8](=[O:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[CH:10]=2)=O)[CH2:3][CH2:2]1.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>[CH:1]1([C:4]2[O:16][C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[CH:10]=3)=[N:7][N:6]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 2715650HCID 2715650, compound

Product 1

HCID 67348658HCID 67348658, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

N′-Cyclopropanecarbonyl-3-iodobenzoic hydrazide (535 mg, 1.62 mmol) obtained in Step 1 was suspended in acetonitrile (20 mL), and the mixture was stirred at 60° C. for 6 hours after adding triphenylphosphine (850 mg, 3.24 mmol), carbon tetrachloride (0.63 mL, 6.48 mmol), and triethylamine (0.45 mL, 3.24 mmol). The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give 2-cyclopropyl-5-(3-iodophenyl)-1,3,4-oxadiazole (499 mg, 99%).

Workup

  1. customThe residue obtained upon concentration under reduced pressure
  2. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-659e61b687594124adfeb7a31f1b3564
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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