Diisopropyl Ether → 2-[O-[N-methyl-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyl]oximino]-3,5,5-trimethylthiazolidin-4-one

HRID 1448080Notes

Reaction equation

HRID 1448080 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][C:18]([CH3:25])([C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH3:19])[C:14](Cl)=[O:15].C(N(CC)CC)C.C(OC(C)C)(C)C>O1CCOCC1>[CH3:12][N:13]([S:17][C:18]([CH3:19])([C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])[CH3:25])[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

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 54024146N-methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyl chlorideHCID 713633892-(Hydroxyimino)-3,5,5-trimethyl-1,3-thiazolidin-4-one

Product 1

HCID 542459562-[O-[N-methyl-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyl]oximino]-3,5,5-trimethylthiazolidin-4-oneYield 39.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Prepared as in Example I by reacting 2.94 g (0.0169 m) of 3,5,5-trimethyl-2-oximino-thiazolidin-4-one, 4.0 g (0.0169 m) of N-methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyl chloride and 1.7 g (0.0169 m) of triethylamine in 200 ml of dioxane. The productcrystallized from isopropyl ether to yield 2.5 g of a white solid, m.p. 112°-114° C.

Workup

  1. customPrepared as in Example I

Sources & evidence

ORD record
ord-ac9267b951534875b221cd95cbc025f2
Source dataset
uspto-grants-1979_12
Patent number
US04179514

Reaction notes

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