Dimethyl Sulfoxide → HCID 18463625, compound

HRID 2231128Notes

Reaction equation

CS(C)=[O:3].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2N=C(C(F)(F)F)N[C:32]=2[C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:24][CH:23]=1)(=O)=O.C(N(CC)CC)C.[OH2:50]>C(Cl)Cl>[CH3:18][S:19][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:3])[C:32]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[O:50])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of dimethylsulphoxide (30 mmol, 2.13 ml) in methylene chloride (90 ml) was cooled to −65° C. Trifluoroacetic acid anhydride (20 mmol, 2.82 ml) was added over 3 minutes, then stirred 10 minutes. 2-Hydroxy-1-[4-(methylthio)phenyl]-2-(3-pyridyl)-ethanone (step 2) (10 mmol, 2.59 g) was suspended in ca 10 ml of methylene chloride and rinsed into the reaction vessel using ca 5 ml additional solvent. After 40 minutes, triethylamine (58 mmol, 8.07 ml) was added. The mixture was warmed to 0° C. over 30 minutes, with continued stirring, then-diluted with water (100 ml) and extracted with ethyl acetate (200, then 2×50 ml). The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and subjected to chromatography (2:1 hexane:ethyl acetate), affording the title compound as a yellow solid (2.43 g, 94%), which was used in the next step.

Workup

washrinsed into the reaction vessel
waitAfter 40 minutes
extractionextracted with ethyl acetate (200
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-438c170d20b24a51bd336c493442bf74
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06426360B1

Reaction notes

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