Dimethyl Sulfide → HCID 22063563, compound

HRID 1828557Notes

Reaction equation

HRID 1828557 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].CSC.[CH:8]1([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:30])=[C:18]([CH2:21][C:22]4[S:23][CH:24]=[C:25]([CH:27]([CH3:29])[CH3:28])[N:26]=4)[CH:19]=3)[C:14](=[O:31])[C:13]([C:32]([O:34]CC)=[O:33])=[C:12]2[N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH2:10][CH2:9]1>ClCCCl.C(Cl)(Cl)Cl>[CH:8]1([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:30])=[C:18]([CH2:21][C:22]4[S:23][CH:24]=[C:25]([CH:27]([CH3:29])[CH3:28])[N:26]=4)[CH:19]=3)[C:14](=[O:31])[C:13]([C:32]([OH:34])=[O:33])=[C:12]2[N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 6451240Aluminum(III) ChlorideHCID 22063507HCID 22063507, compound

Product 1

HCID 22063563HCID 22063563, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of aluminum chloride (266 mg, 2.00 mmol) in 1,2-dichloroethane (4 ml) was added with dimethyl sulfide (0.293 ml, 4.00 mmol) and stirred at 0° C. for 30 minutes. Then, the reaction mixture was added with ethyl 1-cyclopropyl-6-fluoro-7-[(4-isopropyl-1,3-thiazol-2-yl)methyl]-2-morpholino-4-oxo-1,4-dihydro-3-quinolinecar boxylate (51.5 mg, 0.0999 mmol) and refluxed overnight by heating. The reaction mixture was left stand for cooling, diluted with chloroform, washed with 1 N hydrochloric acid, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by preparative TLC (chloroform:methanol=10:1) to obtain the title compound (1.3 mg, 3%).

Workup

  1. temperaturerefluxed overnight
  2. temperatureby heating
  3. waitThe reaction mixture was left stand
  4. temperaturefor cooling
  5. washwashed with 1 N hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe obtained residue was purified by preparative TLC (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-35736636a3f54a32ba9ad54cded121b3
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

Loading…