Triethylamine → 2-[[O-[N-Methyl-N-(4-methylphenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one

HRID 224382Notes

Reaction equation

HRID 224382 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]([CH3:9])([CH3:8])[S:4][C:3]1=[N:10][OH:11].[CH3:12][N:13]([S:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:14](F)=[O:15].C(N(CC)CC)C>O1CCOCC1>[CH3:12][N:13]([S:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:14]([O:11][N:10]=[C:3]1[N:2]([CH3:1])[C:6](=[O:7])[C:5]([CH3:9])([CH3:8])[S:4]1)=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23332987N-Methyl-N(4-Methylphenylthiosulfenyl)Carbamoyl FluorideHCID 713633892-(Hydroxyimino)-3,5,5-trimethyl-1,3-thiazolidin-4-one

Product 1

HCID 536679272-[[O-[N-Methyl-N-(4-methylphenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-[[O-[N-Methyl-N-(4-methylphenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one was prepared according to the procedure described in Example I, by reacting 5.0 g (0.0287 m) of 3,5,5-trimethyl-2-oximino thiazolidin-4-one, 6.64 g (0.028 m) of N-methyl-N-(4-methylphenylthiosulfenyl)carbamoyl fluoride and 2.9 g (0.0287 m) of triethylamine in 50 ml of dioxane. 2-[[O-[N-Methyl-N-(4-methylphenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one was crystallized from ethylacetate-hexane to yield 8.0 g of solid, m.p. 116°-118° C. It was then recrystallized from ethyl acetate isopropyl ether, to yield a solid, m.p. 123°-125° C.

Workup

  1. custom2-[[O-[N-Methyl-N-(4-methylphenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one was crystallized from ethylacetate-hexane

Sources & evidence

ORD record
ord-aaa0567b70354eafb83901a48fc8e5f2
Source dataset
uspto-grants-1980_11
Patent number
US04232035

Reaction notes

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