Diisopropyl Ether → 4-[[O-[N-Methyl-N-(methylthiosulfenyl)carbamoyl]oximino]]-5-methyl-1,3-oxathiolane

HRID 224375Notes

Reaction equation

HRID 224375 reaction equation
[CH3:1][CH:2]1[O:6][CH2:5][S:4][C:3]1=[N:7][OH:8].[CH3:9][N:10]([S:14][S:15][CH3:16])[C:11](F)=[O:12].C(N(CC)CC)C.C(OC(C)C)(C)C>O1CCOCC1>[CH3:9][N:10]([S:14][S:15][CH3:16])[C:11]([O:8][N:7]=[C:3]1[CH:2]([CH3:1])[O:6][CH2:5][S:4]1)=[O:12]

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 20479042N-methyl-N-(methylthiosulfenyl) carbamoyl fluorideHCID 71364792N-(5-Methyl-1,3-oxathiolan-4-ylidene)hydroxylamine

Product 1

HCID 539513834-[[O-[N-Methyl-N-(methylthiosulfenyl)carbamoyl]oximino]]-5-methyl-1,3-oxathiolaneYield 1.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4.22 g (0.032 m) of 5-methyl-4-oximino-1,3-oxathiolane and 5.0 g (0.032 m) of N-methyl-N-(methylthiosulfenyl) carbamoyl fluoride in 25 ml of dioxane was added 3.25 g (0.032 m) of triethylamine. After stirring at room temperature for 19 hrs. the reaction mixture was quenched with 100 ml of water and extracted in ethyl acetate. After the usual work-up it yielded a residual oil. Addition of isopropyl ether resulted in the precipitation of 0.16 g of a solid biscarbamate. The concentrated filtrate was purified by column chromatography to yield 2.97 g of an oil.

Workup

  1. customthe reaction mixture was quenched with 100 ml of water
  2. extractionextracted in ethyl acetate
  3. customAfter the usual work-up it yielded a residual oil

Sources & evidence

ORD record
ord-344b732e97e94e248037819139cdc6ee
Source dataset
uspto-grants-1980_11
Patent number
US04232035

Reaction notes

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