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

HRID 224383Notes

Reaction equation

HRID 224383 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]([Cl: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]([Cl: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 23333002N-methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl fluorideHCID 713633892-(Hydroxyimino)-3,5,5-trimethyl-1,3-thiazolidin-4-one

Product 1

HCID 539010492-[[O-[N-Methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-[[O-[N-Methyl-N-(4-chlorophenylthiosulfenyl)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, 7.22 g (0.0287 m) of N-methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl fluoride and 2.9 g (0.0287 m) of triethylamine in 50 ml of dioxane. 2-[[O-[N-Methyl-N-(4-chlorophenylthiosulfenyl)carbamoyl]oximino]]-3,5,5-trimethylthiazolidin-4-one was crystallized from isopropyl ether to yield 5.9 g of a white solid, m.p. 74°-76° C.

Workup

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

Sources & evidence

ORD record
ord-4c4caf07d5034b9ab3b74b9f120df43e
Source dataset
uspto-grants-1980_11
Patent number
US04232035

Reaction notes

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