Methyl[(trichloromethyl)sulfanyl]carbamyl fluoride → 5,5-Dimethyl-2-ethylimino-4-[[O-[N-methyl-N-(trichloromethanesulfenyl)carbamoyl]oximino]]-1,3-dithiolane

HRID 263232Notes

Reaction equation

HRID 263232 reaction equation
[CH3:1][C:2]1([CH3:12])[S:6][C:5](=[N:7][CH2:8][CH3:9])[S:4][C:3]1=[N:10][OH:11].[CH3:13][N:14]([S:18][C:19]([Cl:22])([Cl:21])[Cl:20])[C:15](F)=[O:16]>O1CCOCC1.O>[CH3:12][C:2]1([CH3:1])[S:6][C:5](=[N:7][CH2:8][CH3:9])[S:4][C:3]1=[N:10][O:11][C:15](=[O:16])[N:14]([CH3:13])[S:18][C:19]([Cl:22])([Cl:21])[Cl:20]

Participants

5

Reactant 2

HCID 12836648Methyl[(trichloromethyl)sulfanyl]carbamyl fluoride2×HCID 859767545,5-Dimethyl-2-ethylimino-4-oximino-1,3-dithiolane

Product 1

HCID 543127205,5-Dimethyl-2-ethylimino-4-[[O-[N-methyl-N-(trichloromethanesulfenyl)carbamoyl]oximino]]-1,3-dithiolaneYield 57.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3.5 grams (0.017m) of 5,5-dimethyl-2-ethylimino-4-oximino-1,3-dithiolane (XXIII) and 3.84 grams (0.017m) of N-methyl-N-trichloromethanesulfenyl carbamoyl fluoride in 75 ml of dioxane, was added dropwise with stirring 1.71 grams (0.017m) of triethylamine. After allowing the reaction mixture to stand at room temperature for 16 hours it was diluted with 250 ml of cold water and was extracted in ethylacetate. The organic extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to a residual oil which crystallized on the addition of isopropyl ether and hexane, to afford 4.0 grams of a white solid. m.p. 69°-71° C.

Workup

  1. extractionwas extracted in ethylacetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure to a residual oil which
  6. customcrystallized on the addition of isopropyl ether and hexane

Sources & evidence

ORD record
ord-e38e112a826a47ed8f9ce78c31a4ee39
Source dataset
uspto-grants-1979_05
Patent number
US04156731

Reaction notes

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