Hexachloroethane → 5-(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)-2-methylphenol

HRID 2081103Notes

Reaction equation

HRID 2081103 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([OH:18])[CH:12]=2)=O)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(Cl)(Cl)Cl>C(#N)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]2[O:19][C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([OH:18])[CH:12]=3)=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 596497183-hydroxy-4-methyl-benzoic acid N'-(4-chloro-benzoyl)-hydrazide

Product 1

HCID 596497245-(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)-2-methylphenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-hydroxy-4-methyl-benzoic acid N′-(4-chloro-benzoyl)-hydrazide (1.28 g, 4.20 mmol) (from Example 44 supra) in acetonitrile (20 mL) was added diisopropylethylamine (4.4 mL, 25.2 mmol) and triphenylphosphine (2.21 g, 8.40 mmol). After stirring 5 minutes, hexachloroethane (1.49 g, 6.30 mmol) (Aldrich) was added and the mixture was allowed to stir for 1 day at room temperature. The solvent was evaporated. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (1×). The combined organic phase washed with water and brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography eluting with 0-60% ethyl acetate in hexanes to give 5-[5-(4-chloro-phenyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol. (Yield 0.34 g, 28%).

Workup

  1. stirringto stir for 1 day at room temperature
  2. customThe solvent was evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous phase was extracted with ethyl acetate (1×)
  5. washThe combined organic phase washed with water and brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with 0-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-69a6041f3d7c496296b6c04e14a769f3
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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