Diethyl Ether → 3-dimethylthiocarbamoylpyridine

HRID 2121199Notes

Reaction equation

HRID 2121199 reaction equation
O[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][N:9]([CH3:13])[C:10](Cl)=[S:11].CCOCC>CN(C=O)C>[CH3:8][N:9]([CH3:13])[C:10]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[S:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 79713-HydroxypyridineHCID 27871Dimethylthiocarbamoyl chloride

Product 1

HCID 122356893-dimethylthiocarbamoylpyridineYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution in DMF (50 mL) of 3-hydroxypyridine (4.76 g, 50 mmol) was added 1,1-diazabicyclo[2.2.2]octane (6.80 g, 150 mmol) and dimethylthiocarbamoyl chloride (18.5 g, 150 mmol) and the reaction mixture was stirred for 0.5 hours at ambient temperature and 18 hours at 55° C. The reaction mixture was cooled to ambient temperature and poured into ether. The ethereal solution was washed with aqueous 2N sodium hydroxide (2×), water (2×) and brine, dried, filtered and concentrated in vacuo. Chromatography on silica gel (1:1 ethyl acetate-hexane) gave 3-dimethylthiocarbamoylpyridine (5.46 g).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washThe ethereal solution was washed with aqueous 2N sodium hydroxide (2×), water (2×) and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-563542ea78324e918b6e684ae9a78cb7
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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