Chloroform → N-[2,2-dimethyl-5-(2-{4-[5-(4-methylbenzoyl)-2-thienyl]phenyl}ethyl)-1,3-dioxan-5-yl]acetamide

HRID 1641572Notes

Reaction equation

HRID 1641572 reaction equation
[OH:1][CH:2]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)[C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]3([NH:24][C:25](=[O:27])[CH3:26])[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C1(C)C=CC([Bi](Cl)(Cl)(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.N12CCCN=C1CCCCC2.C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:22][C:19]1([CH3:23])[O:18][CH2:17][C:16]([NH:24][C:25](=[O:27])[CH3:26])([CH2:15][CH2:14][C:11]2[CH:10]=[CH:9][C:8]([C:6]3[S:7][C:3]([C:2](=[O:1])[C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)=[CH:4][CH:5]=3)=[CH:13][CH:12]=2)[CH2:21][O:20]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11261392Tri(p-tolyl)bismuth dichlorideHCID 57624590N-{5-[2-(4-{5-[hydroxy(4-methylphenyl)methyl]-2-thienyl}phenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide

Product 1

HCID 57624584N-[2,2-dimethyl-5-(2-{4-[5-(4-methylbenzoyl)-2-thienyl]phenyl}ethyl)-1,3-dioxan-5-yl]acetamideYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{5-[2-(4-{5-[hydroxy(4-methylphenyl)methyl]-2-thienyl}phenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide (0.35 g) in methylene chloride (5 mL) were added tri(p-tolyl)bismuth dichloride (393 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (108 mg) at room temperature, and the mixture was stirred at the same temperature for 2 hr. Chloroform was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.22 g) as brown crystals.

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ed63bf5a12d486f83abff7d1906a0ec
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

Loading…