Hexachloroethane → HCID 68936932, compound

HRID 2218748Notes

Reaction equation

HRID 2218748 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6](=[CH:14][C:15]3[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=3)[C:7]3[CH:8]=[CH:9][S:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.[Li]CCCC.[Cl:29]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:29][C:9]1[S:10][C:11]2[CH2:12][CH2:13][C:4]3[CH:3]=[C:2]([Cl:1])[CH:23]=[CH:22][C:5]=3[C:6](=[CH:14][C:15]3[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=3)[C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 68933751HCID 68933751, compoundHCID 178418339Butyllithium

Product 1

HCID 68936932HCID 68936932, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 553 (above), using 3-(7-chloro-9,10-dihydro-1-thia-benzo[f]azulen-4-ylidenemethyl)-phenylamine, n-BuLi in hexanes, THF, and hexachloroethane. Purify the crude residue by column chromatography (5% to 20% to 30% EtOAc:hexanes) to give title compound as an oil (21%) along with recovered starting material: 1H NMR (CDCl3, 400 MHz) δ 2.06-3.02 (m, 4 H), 3.53 (br s, 2 H), 6.32 (s, 1 H), 6.38 (d, J=7.2 Hz, 1 H), 6.48 (dd, J=7.2 Hz, 1.6 Hz, 1 H), 6.79 (s, 1 H), 6.93-6.96 (m, 3 H), 7.02 (dd, J=8.2 Hz, 2.2 Hz, 1 H), 7.27 (d, J=8.2 Hz, 1 H). TLC Rf=0.55 (30% EtOAc:hexanes).

Workup

  1. customPurify the crude residue by column chromatography (5% to 20% to 30% EtOAc:hexanes)

Sources & evidence

ORD record
ord-6458b24a5aa14ae894bbd57e353b508c
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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