Dimethyl Disulfide → HCID 15044963, compound

HRID 654621Notes

Reaction equation

HRID 654621 reaction equation
CS[S:3][CH3:4].Br[C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([O:18][CH3:19])[C:13]=1[O:14][CH2:15][CH2:16][CH3:17])[CH:9]=[O:10]>N1C=CC(C)=CC=1C.[Cu]>[CH3:19][O:18][C:12]1[CH:11]=[C:8]([CH:7]=[C:6]([S:3][CH3:4])[C:13]=1[O:14][CH2:15][CH2:16][CH3:17])[CH:9]=[O:10]

Participants

5

Reactant 2

HCID 12232Dimethyl DisulfideHCID 20640193-bromo-5-methoxy-4-propoxybenzaldehyde

Product 1

HCID 15044963HCID 15044963, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 79362,4-DimethylpyridineSolvent

Procedure

50 (0.56 mole) of methyl disulfide in 400 ml of 2.4-lutidine was added 46 g (0.72 mole) of copper. The mixture was heated at 140 ° for 3 hours. The solution was cooled to room temperature and 74.90 g (0.56 mole) of 3-bromo-5-methoxy-4-propoxybenzaldehyde was then added. The mixture was refluxed for 16 hours at 175° C. The solution was filtered and the filtrate was concentrated to dryness. The product was purified by flash column chromatography first then recrystallized from hexane to give 17.01 g (26% yield) of 3-methoxy-5-methylthio-4-propoxybenzaldehyde as a white solid. m.p. 64°-66° C. NMR (CDCl3): δ 1.1 (t, 3H, term CH3), 1.79 (m, 2H, OCH2CH2CH3), 2.47 (s, 3H, SCH3), 3.87 (s, 3H, OCH3), 4.05 (t, 2H, OCH2CH2CH3), 7.20 (S, 2H, Ar-e,uns/H/ ), ##STR25##

Workup

  1. temperatureThe mixture was heated at 140 ° for 3 hours
  2. temperatureThe mixture was refluxed for 16 hours at 175° C
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe product was purified by flash column chromatography first
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-f865378395994a25819c8ea303a31edd
Source dataset
uspto-grants-1992_07
Patent number
US05132463

Reaction notes

Loading…