Methyl iodide → HCID 54393995, compound

HRID 1253234Notes

Reaction equation

HRID 1253234 reaction equation
[CH2:1](N(CC)CC)C.[F:8][C:9]([F:27])([F:26])[C:10]1[S:14][C:13]([NH:15][C:16](=[S:25])[S:17][CH2:18][CH2:19][C:20]([F:24])=[C:21]([F:23])[F:22])=[N:12][N:11]=1.CI>CN(C)C=O.O>[CH3:1][N:15]([C:13]1[S:14][C:10]([C:9]([F:8])([F:26])[F:27])=[N:11][N:12]=1)[C:16](=[S:25])[S:17][CH2:18][CH2:19][C:20]([F:24])=[C:21]([F:23])[F:22]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 54345874HCID 54345874, compound

Product 1

HCID 54393995HCID 54393995, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.69 gram, 0.0068 mole) was added to a stirred solution of (3,4,4-trifluoro-3-butenyl) N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-dithiocarbamate (2.0 grams, 0.0057 mole) in dimethylformamide (5.7 ml) at ambient temperature. After addition was complete, the reaction mixture stirred for one hour and was then cooled to 0° C. Methyl iodide (1.0 gram, 0.0063 mole) was added to the cooled mixture. After warming to ambient temperature, the reaction mixture was stirred overnight. The reaction mixture was diluted with water (200 ml) and extracted three times with diethyl ether. The combined extracts were washed with 10% aqueous hydrochloric acid. The dried (magnesium sulfate) extracts were concentrated under reduced pressure, leaving a residue. This residue was passed through a column of silica gel, eluting with hexane to yield the first product (3,4,4-trifluoro-3-butenyl) N-(methyl)-N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)dithiocarbamate (0.45 gram) as a yellow oil. Eluting solvent was then changed to hexane:ethyl acetate (1:1) to yield the second product methyl(3,4,4-trifluoro-3-butenyl) N-(5-trifluoromethyl- 1,3,4-thiadiazol-2-yl)imidodithiocarbonate (0.96 gram) as an orange oil. The NMR spectra were consistent with the proposed structures.

Workup

  1. additionAfter addition
  2. temperatureAfter warming to ambient temperature
  3. stirringthe reaction mixture was stirred overnight
  4. extractionextracted three times with diethyl ether
  5. washThe combined extracts were washed with 10% aqueous hydrochloric acid
  6. dry with materialThe dried (magnesium sulfate) extracts
  7. concentrationwere concentrated under reduced pressure
  8. customleaving a residue
  9. washeluting with hexane

Sources & evidence

ORD record
ord-12c079c0e38f42b8ae49008b971d3f71
Source dataset
uspto-grants-1988_05
Patent number
US04748186

Reaction notes

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