Hexachloroethane → HCID 68933583, compound

HRID 2218747Notes

Reaction equation

HRID 2218747 reaction equation
[S:1]1[C:10]2[CH2:9][CH2:8][C:7]3[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=3[C:5](=[CH:15][C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)[C:4]=2[CH:3]=[CH:2]1.[Cl:23]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:23][C:2]1[S:1][C:10]2[CH2:9][CH2:8][C:7]3[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=3[C:5](=[CH:15][C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6214HexachloroethaneHCID 68938678HCID 68938678, compound

Product 1

HCID 68933583HCID 68933583, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add 2.2 equiv of n-BuLi-hexanes dropwise to a solution of 3-(9,10-dihydro-1-thia-benzo[f]azulen-4-ylidenemethyl)-phenylamine in THF (0.1 M) at 0° C. under Ar. Stir the resultant dark solution for 1 h before adding 2.5 equiv of hexachloroethane in THF. Stir for 2 h, quench with excess water, and acidify to neutral pH. Extract the aqueous layer with diethyl ether (3×) and then dry (MgSO4) and concentrate the combined organic layers under reduced pressure. Purify the crude residue by column chromatography (0% to 2% to 20% EtOAc:hexanes) to give title compound as an oil (22%) along with recovered starting material: HPLC (ISO80-20A) t=1.903 (90%). MS (APCI): 338 (M+1).

Workup

  1. stirringStir for 2 h
  2. customquench with excess water
  3. extractionExtract the aqueous layer with diethyl ether (3×)
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate the combined organic layers under reduced pressure
  6. customPurify the crude residue by column chromatography (0% to 2% to 20% EtOAc:hexanes)

Sources & evidence

ORD record
ord-82b4a0835e4140c19ed53d783eccb0ef
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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