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

HRID 224381Notes

Reaction equation

HRID 224381 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][CH:22]=[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][CH:22]=[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 23332999N-Methyl-N(Phenylthiosulfenyl)Carbamoyl FluorideHCID 713633892-(Hydroxyimino)-3,5,5-trimethyl-1,3-thiazolidin-4-one

Product 1

HCID 543220962-[[O-[N-Methyl-N-(phenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-[[O-[N-Methyl-N-(phenylthiosulfenyl)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-oximinothiazolidin-4-one, 6.24 g (0.0287 m) of N-methyl-N-(phenylthiosulfenyl)carbamoyl fluoride and 2.9 g (0.0287 m) of triethylamine in 100 ml of dioxane. 2-[[O-[N-Methyl-N-(phenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one was crystallized from isopropyl ether to yield 7.0 g of a white solid. m.p. 73°-74° C.

Workup

  1. custom2-[[O-[N-Methyl-N-(phenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-025e6f8429b540438658ecc421358d36
Source dataset
uspto-grants-1980_11
Patent number
US04232035

Reaction notes

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