Triethylamine → 4-[[O-[N-Methyl-N-(4-methylphenylthiosulfenyl)carbamoyl]oximino]]-5-methyl-1,3-oxathiolane

HRID 224377Notes

Reaction equation

HRID 224377 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][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[C:11](F)=[O:12].C(N(CC)CC)C>O1CCOCC1>[CH3:9][N:10]([S:14][S:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[C:11]([O:8][N:7]=[C:3]1[CH:2]([CH3:1])[O:6][CH2:5][S:4]1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23332987N-Methyl-N(4-Methylphenylthiosulfenyl)Carbamoyl FluorideHCID 71364792N-(5-Methyl-1,3-oxathiolan-4-ylidene)hydroxylamine

Product 1

HCID 540223204-[[O-[N-Methyl-N-(4-methylphenylthiosulfenyl)carbamoyl]oximino]]-5-methyl-1,3-oxathiolane

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[[O-[N-Methyl-N-(4-methylphenylthiosulfenyl)carbamoyl]oximino]]-5-methyl-1,3-oxathiolane was prepared by the procedure described in Example I by reacting 4.0 g (0.03 m) of 5-methyl-4-oximino-1,3-oxathiolane, 6.95 g (0.03 m) of N-methyl-N-(4-methylphenylthiosulfenyl) carbamoyl fluoride and 3.07 g (0.03 m) of triethylamine in 50 ml of dioxane. The crude residual oil (7.3 g) was purified by dry column chromatography using silica gel.

Workup

  1. customThe crude residual oil (7.3 g) was purified
  2. customby dry column chromatography

Sources & evidence

ORD record
ord-8816d04edd0c46de9d22c35956193111
Source dataset
uspto-grants-1980_11
Patent number
US04232035

Reaction notes

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