Dimethylformamide → 6,6-difluoro-5-methyl-5-hexenyl N,N-dimethyldithiocarbamate

HRID 917404Notes

Reaction equation

HRID 917404 reaction equation
CN(C)C=O.CS(O[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])(=O)=O.O.O.[CH3:22][N:23]([CH3:27])[C:24](=[S:26])[S-:25].[Na+]>O>[CH3:22][N:23]([CH3:27])[C:24](=[S:25])[S:26][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:17])[F:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 230203716,6-Difluoro-5-methyl-5-hexenyl methanesulfonateHCID 23693613Sodium dimethyldithiocarbamate dihydrate

Product 1

HCID 230202846,6-difluoro-5-methyl-5-hexenyl N,N-dimethyldithiocarbamateYield 51.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 100 ml of N,N-dimethylformamide, 4.56 g (20 mmol) of 6,6-difluoro-5-methyl-5-hexenyl methanesulfonate and 4.70 g (26 mmol) of sodium dimethyldithiocarbamate dihydrate were dissolved, followed by stirring at 100° C. for 3 hours. The reaction liquid was poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentrating under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10) to obtain 2.60 g (yield: 51%) of 6,6-difluoro-5-methyl-5-hexenyl N,N-dimethyldithiocarbamate.

Workup

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. concentrationconcentrating under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-c50415224a2f482d976daa0add79a524
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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