Dimethyl Disulfide → [2-(4-Methyl-5-thiazolyl)ethyl]-methyl-disulphide

HRID 66065Notes

Reaction equation

HRID 66065 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][SH:9].[CH3:10][S:11]SC>[H-].[Na+]>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][CH2:8][S:9][S:11][CH3:10]

Participants

4

Reactant 2

HCID 12232Dimethyl DisulfideHCID 186900032-(4-Methyl-1,3-thiazol-5-yl)ethane-1-thiol

Product 1

HCID 20306425[2-(4-Methyl-5-thiazolyl)ethyl]-methyl-disulphideYield 60.4%

Reagents, catalysts & solvents 1

HCID 24758Sodium hydrideCatalyst

Procedure

A mixture of 8.26 g (0.052 mol) of 2-(4-methyl-5-thiazolyl)-ethyl-mercaptan and 33.07 g (0.208 mol) of dimethyldisulphide is treated with 50 mg of sodium hydride (50% dispersion in oil) and the mixture is heated to reflux for 4 hours. The mixture is then left to cool, filtered over 10 g of aluminium oxide (activity I, neutral), which is back-washed with ether, and concentrated in a vacuum. The resulting crude product (9.5 g) is distilled through a Hempel column under a high vacuum, there being obtained 6.45 g of [2-(4-methyl-5-thiazolyl)-ethyl]-methyl-disulphide. Boiling point 104°-110°/0.02 mm Hg; nD20 = 1.5944; purity: 99%. IR (liq.): bands inter alia at 3100, 2960, 1545, 1415, 1220, 955, 1005, 840, 795 cm-1.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 4 hours
  3. waitThe mixture is then left
  4. temperatureto cool
  5. filtrationfiltered over 10 g of aluminium oxide (activity I, neutral), which
  6. washis back-washed with ether
  7. concentrationconcentrated in a vacuum
  8. distillationThe resulting crude product (9.5 g) is distilled through a Hempel column under a high vacuum

Sources & evidence

ORD record
ord-f5cb927177a041298154da5508183217
Source dataset
uspto-grants-1978_12
Patent number
US04130562

Reaction notes

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