Water → Isamoxole

HRID 613996Notes

Reaction equation

C([C:5]([CH3:10])([CH3:9])[C:6]([NH2:8])=[O:7])CCC.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].[CH3:16][C:17]1[N:18]=[C:19](S(C)=O)[O:20][CH:21]=1.O>C1COCC1>[CH2:11]([N:8]([C:19]1[O:20][CH:21]=[C:17]([CH3:16])[N:18]=1)[C:6](=[O:7])[CH:5]([CH3:9])[CH3:10])[CH2:12][CH2:13][CH3:14]

Participants

Conditions

Temperature: -20 °C

Procedure

n-Butyl-isobutyramide (0.99 g, 0.0069 m) in dry THF (10 ml) was cooled to -20° C. under nitrogen during the dropwise addition of a 1.445 M solution of n-butyl lithium (4.8 ml, 0.0069 m). The mixture was stirred for 20 minutes at -20° C. and then 4-methyl-2-methylsulphinyloxazole (1.0 g, 0.0068 m) in dry THF (10 ml) was added rapidly and the mixture allowed to warm to 0° C. It was stirred at this temperature for 11/2 hours then allowed to warm to room temperature and stirred for a further 1/2 hour. The mixture was hydrolysed with water and the solvent was evaporated under reduced pressure. The residue was extracted with diethyl ether and the extract was evaporated. The resulting oil was chromatographed on silica using ether/hexane. The compound was distilled in vacuo to give the title compound as a colourless oil 1.21 g, (78%), b.p. (airbath) 70° C. at 0.01 mm.

Workup

temperatureto warm to 0° C
stirringIt was stirred at this temperature for 11/2 hours
temperatureto warm to room temperature
stirringstirred for a further 1/2 hour
customthe solvent was evaporated under reduced pressure
extractionThe residue was extracted with diethyl ether
customthe extract was evaporated
customThe resulting oil was chromatographed on silica
distillationThe compound was distilled in vacuo

Sources & evidence

ORD record: ord-54f32ab7f6744aa99fcfa55533e31fbd
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04143047

Reaction notes

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