Triethylamine → 1,3-Dithiolan-2-one, O-((((1,1-dimethylethyl)dithio)methylamino)carbonyl)oxime

HRID 224384Notes

Reaction equation

HRID 224384 reaction equation
[N:1](=[C:3]1[S:7][CH2:6][CH2:5][S:4]1)[OH:2].[CH3:8][N:9]([S:13][S:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:10](F)=[O:11].C(N(CC)CC)C>O1CCOCC1>[CH3:8][N:9]([S:13][S:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]([O:2][N:1]=[C:3]1[S:7][CH2:6][CH2:5][S:4]1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 124040782-Oximino-1,3-dithiolaneHCID 20399612N-methyl-N-(tert-butylthiosulfenyl)carbamoyl fluoride

Product 1

HCID 30596081,3-Dithiolan-2-one, O-((((1,1-dimethylethyl)dithio)methylamino)carbonyl)oxime

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-[[O-[N-Methyl-N-(tert-butylthiosulfenyl)carbamoyl]oximino]]-1,3-dithiolane was prepared according to the procedure described in Example I, by reacting 2.9 g (0.0214 m) of 2-oximino-1,3-dithiolane, 4.23 g (0.0214 m) of N-methyl-N-(tert-butylthiosulfenyl)carbamoyl fluoride and 2.17 g (0.0214 m) of triethylamine in 50 ml of dioxane. 2-[[O-[N-Methyl-N-tert-butylthiosulfenyl)carbamoyl]oximino]]-1,3-dithiolane crystallized from methylene chloride isopropyl ether to yield 4.0 g of a white solid. It was then recrystallized from ethyl acetate to yield a solid, m.p. 112°-114° C.

Workup

  1. custom2-[[O-[N-Methyl-N-tert-butylthiosulfenyl)carbamoyl]oximino]]-1,3-dithiolane crystallized from methylene chloride isopropyl ether

Sources & evidence

ORD record
ord-badd9a2a625a4508953c96755c87c88a
Source dataset
uspto-grants-1980_11
Patent number
US04232035

Reaction notes

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