Chloride → HCID 67426036, compound

HRID 1515377Notes

Reaction equation

HRID 1515377 reaction equation
[Cl-].[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]1([S:15]/[CH:16]=[C:17]2/[C:18](=[O:23])[O:19][CH2:20][CH2:21][CH2:22]/2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>C(Cl)Cl>[OH:19][CH2:20][CH2:21][CH2:22]/[C:17](=[CH:16]\[S:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)/[C:18]([NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:23]

Participants

6

Reactant 4

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 6115AnilineHCID 67426961HCID 67426961, compound

Product 1

HCID 67426036HCID 67426036, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.4 ml of diethylalumiun chloride (1 mol/1 of hexane solution) was added to 10 ml of methylene chloride solution including 0.6 g of aniline at room temperature. After stirring for 5 minutes, methylene chloride solution including 1.28 g of (E)-3-(phenylthiomethylene)tetrahydro-2H-pyran-2-one was dropped into the resulting solution. After stirring at room temperature for 2 hours, the solution was added with 10% hydrochloric acid, then stirred at room temperature for 30 minutes. The solution was extracted with ethyl acetate, and the organic layer was washed with brine, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.64 g of the title compound.

Workup

  1. customat room temperature
  2. additionwas dropped into the resulting solution
  3. stirringAfter stirring at room temperature for 2 hours
  4. stirringstirred at room temperature for 30 minutes
  5. extractionThe solution was extracted with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bfd2ba173f7f4c2f8bfc64640da448ff
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

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