Methanol → HCID 54158845, compound

HRID 1732445Notes

Reaction equation

HRID 1732445 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:12][S:13][CH2:14][S:15]([CH3:17])=[O:16].CO.[OH-].C[N+](C)(C)CC1C=CC=CC=1>O1CCCC1.C(O)(=O)C.O>[CH3:17][S:15]([C:14]([S:13][CH3:12])=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([N:2]([CH3:11])[CH3:1])=[CH:4][CH:5]=1)=[O:16]

Participants

8

Reactant 4

HCID 887MethanolHCID 74794-(Dimethylamino)BenzaldehydeHCID 66854Benzyltrimethylammonium hydroxideHCID 99129Methyl (methylsulfinyl)methyl sulfide

Product 1

HCID 54158845HCID 54158845, compoundYield 60.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

p-Dimethylaminobenzaldehyde (12.953 g) was dissolved in 30 ml of tetrahydrofuran, and 18.428 g of FAMSO and 12 ml of a 40% methanol solution of trimethylbenzylammonium hydroxide were added. The mixture was heated under reflux for 40 hours. Water was added, and the reaction mixture was acidified with acetic acid and then extracted with methylene chloride. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using methylene chloride/ethyl acetate as an eluant, and then recrystallized from diethyl ether to afford 13.492 g of 1-methylsulfinyl-1-methylthio-2-(p-dimethylaminophenyl)ethylene.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 40 hours
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column
  8. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-79d9b27effa64033bfcfab545112aadc
Source dataset
uspto-grants-1980_12
Patent number
US04237298

Reaction notes

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