4-Aminobenzaldehyde → HCID 54203179, compound

HRID 1732444Notes

Reaction equation

HRID 1732444 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[CH3:12][S:13][CH2:14][S:15]([CH3:17])=[O:16].[Cl-].[NH4+]>>[CH3:17][S:15]([C:14]([S:13][CH3:12])=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([NH2:3])=[CH:5][CH:6]=1)=[O:16]

Participants

5

Reactant 4

HCID 111584-AminobenzaldehydeHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 99129Methyl (methylsulfinyl)methyl sulfide

Product 1

HCID 54203179HCID 54203179, compoundYield 62.3%

Conditions

Temperature
80 °C

Procedure

Flakes of sodium hydroxide (55 mg) were added to a mixture of 201 mg of p-aminobenzaldehyde and 798 mg of FAMSO, and the mixture was stirred at 80° C. for 30 minutes. After adding 50 ml of a saturated aqueous solution of ammonium chloride, the reaction mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using methylene chloride as an eluant to afford oil-containing orange crystals. Washing of the crystals with acetone afforded 235 mg of 1-methylsulfinyl-1-methylthio-2-(p-aminophenyl)ethylene as pale yellow crystals in a yield of 62%. Samples for analysis were obtained as colorless crystals by recrystallization.

Workup

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on a silica gel column
  5. customto afford
  6. additionoil-containing orange crystals
  7. washWashing of the crystals with acetone

Sources & evidence

ORD record
ord-a4329f82d3464d909fd89bda2295a09c
Source dataset
uspto-grants-1980_12
Patent number
US04237298

Reaction notes

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