Triethylamine → 5-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(N-methylfluoroformamidothio)-N-methylcarbamoyl]oxime

HRID 1981374Notes

Reaction equation

C(N(CC)CC)C.[N:8](=[C:10]1[S:14][C:13]([CH3:16])([CH3:15])[N:12]=[C:11]1[CH3:17])[OH:9].[CH3:18][N:19]([S:23][N:24]([CH3:28])[C:25](F)=[O:26])[C:20]([F:22])=[O:21]>C1(C)C=CC=CC=1>[CH3:18][N:19]([S:23][N:24]([CH3:28])[C:25]([O:9][N:8]=[C:10]1[S:14][C:13]([CH3:16])([CH3:15])[N:12]=[C:11]1[CH3:17])=[O:26])[C:20]([F:22])=[O:21]

Participants

Conditions

Temperature: -50 °C

Procedure

8.3 ml of triethylamine are added dropwise to a suspension of 8.59 g of 5-oxo-2,2,4-trimethyl-3-thiazoline oxime in a solution of 10.0 g of bis-(N-methyl-N-fluorocarbonylamino)sulfide in 100 ml of absolute toluene, cooled to -50° C. The resulting clear solution is allowed to warm slowly to 0° C. during 11/2 hours, during which time a crystalline product is precipitated. The reaction mixture is poured into ice-cold brine and extracted with ethyl acetate. After drying the organic phase over anhydrous sodium sulfate and evaporating it, the resulting residue is purified by chromatography on silica gel (eluent:ethyl acetate/n-hexane 1:1). Crystallization from ethyl acetate/n-hexane yields 5-oxo-2,2,4-trimethyl-3-thiazoline O-[N-(N-methylfluoroformamidothio)-N-methylcarbamoyl]oxime, m.p. 77°-79° C.

Workup

temperatureto warm slowly to 0° C. during 11/2 hours
customduring which time a crystalline product is precipitated
additionThe reaction mixture is poured into ice-cold brine
extractionextracted with ethyl acetate
dry with materialAfter drying the organic phase over anhydrous sodium sulfate
customevaporating it
customthe resulting residue is purified by chromatography on silica gel (eluent:ethyl acetate/n-hexane 1:1)
customCrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-2f5c88dbb8f24077b1f30030dd6ef7ad
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04514566

Reaction notes

Loading…