Dichloromethane → HCID 11740455, compound

HRID 2181841Notes

Reaction equation

HRID 2181841 reaction equation
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:2].B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)(=[O:20])=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 22482343HCID 22482343, compound

Product 1

HCID 11740455HCID 11740455, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The title compound was prepared from 6-ethyl-5-[(4-methoxyphenyl)sulfonyl]-9-methyl-5,6-dihydrophenanthridine (0.67 g, 1.7 mmol), tetrabutylammonium iodide (1.5 g, 4.1 mmol), and 1 M boron trichloride in dichloromethane (11.9 mL, 11.9 mmol) according to the procedure and in the same manner as described in Example 35, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (3:7 to 1:1 gradient), followed by trituration from a mixture of ethyl acetate-hexane, to yield 4-[(6-ethyl-9-methylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.23 g, 36%), m.p. 167-170° C.;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (3:7 to 1:1 gradient)
  3. additionfollowed by trituration from a mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-30a845cfd49241b0ad348488446fa7c2
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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