Diethyl Ether → N-Methyl-N-(4-methyl-1,3-oxazol-2-yl)acetamide

HRID 613992Notes

Reaction equation

[CH3:1][NH:2][C:3](=[O:5])[CH3:4].[H-].[K+].C(S([C:16]1[O:17][CH:18]=[C:19]([CH3:21])[N:20]=1)=O)CCCCC.CCOCC>CN(P(N(C)C)(N(C)C)=O)C>[CH3:1][N:2]([C:16]1[O:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:3](=[O:5])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

N-Methyl-acetamide (1.02 g, 0.0140 m) in HMPA (10 ml) was stirred at 50° C. under nitrogen during the portionwise addition of 50% potassium hydride/oil dispersion (1.12 g, 0.0140 m). After the addition, the mixture was warmed to 100° C. and 2-n-hexylsulphinyl-4-methyloxazole (3.0 g, 0.0139 m) in HMPA (10 ml) was added and the mixture stirred at 100° C. for 5 hours. The mixture was then hydrolysed with water, solvent removed in vacuo and the product isolated by column chromatography on silica using ether. Recrystallisation from diethyl ether/hexane at -20° C. gave the title product as colourless needles, m.p. 27°-29° C.

Workup

additionAfter the addition
customhydrolysed with water, solvent removed in vacuo
customthe product isolated by column chromatography on silica
customRecrystallisation from diethyl ether/hexane at -20° C.

Sources & evidence

ORD record: ord-b51de74d26034ae4b454d880a32b14f3
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04143047

Reaction notes

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