Triethylamine → 3,5,5-Trimethyl-2-[[-O-[N-methyl-N-(2-methyl-1,3-dichloro-2-propanesulfenyl)carbamoyl] oximino]]-4-thiazolidinone

HRID 1980107Notes

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]([CH3:23])([CH2:21][Cl:22])[CH2:19][Cl:20])[C:14](F)=[O:15].C(N(CC)CC)C>O1CCOCC1.O.C(OC(=O)C)C>[CH3:1][N:2]1[C:6](=[O:7])[C:5]([CH3:9])([CH3:8])[S:4][C:3]1=[N:10][O:11][C:14](=[O:15])[N:13]([CH3:12])[S:17][C:18]([CH3:23])([CH2:19][Cl:20])[CH2:21][Cl:22]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 3.28 g of 3,5,5-trimethyl-2-oximino-4-thiazolidinone and 5.0 g of N-methyl-N-(2-methyl-1,3-dichloro-2-propanesulfenyl)carbamoyl fluoride in 75 ml of dioxane, was added dropwise with stirring 2.18 g of triethylamine. The spontaneous exotherm raised the temperature to 30° C. After following the reaction mixture to stand at room temperature for 16 hours, the reaction mixture was diluted with 300 ml of water. The product was isolated in ethylacetate and purified by column chromatography over silica gel to yield 3.0 g of a white solid. m.p. 91°-92° C.

Workup

custompurified by column chromatography over silica gel

Sources & evidence

ORD record: ord-2a716f53d2524365aced58d636dc940e
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04485113

Reaction notes

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