Hexachloroethane → HCID 59649713, compound

HRID 2081098Notes

Reaction equation

HRID 2081098 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([OH:21])[CH:15]=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:3]=[CH:4][C:5]([CH2:8][C:9]2[O:22][C:13]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([OH:21])[CH:15]=3)=[N:12][N:11]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 596497123-hydroxy-4-methyl-benzoic acid N'-[2-(4-chloro-phenyl)-acetyl]-hydrazide

Product 1

HCID 59649713HCID 59649713, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-hydroxy-4-methyl-benzoic acid N′-[2-(4-chloro-phenyl)-acetyl]-hydrazide (0.91 g, 2.85 mmol) (from Example 39 supra) in acetonitrile (20 mL) was added diisopropylethylamine (3.0 mL, 17.1 mmol) and triphenylphosphine (1.50 g, 5.70 mmol). After stirring 5 minutes, hexachloroethane (1.01 g, 4.28 mmol) (Aldrich) was added and the mixture was allowed to stir for 2 days 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 was washed with water and brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to 5-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol. (Yield 0.68 g, 79%).

Workup

  1. stirringto stir for 2 days 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 was washed with water and brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with 20% ethyl acetate in hexanes to 5-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol

Sources & evidence

ORD record
ord-7e222c3fca744f9395599d4e0d266056
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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