Water → N-(Butan-2-yl)-N-(4-methyl-1,3-oxazol-2-yl)butanamide

HRID 613995Notes

Reaction equation

[CH:1]([NH:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9])([CH2:3][CH3:4])[CH3:2].C([Li])CCC.[CH3:16][C:17]1[N:18]=[C:19](S(C)=O)[O:20][CH:21]=1.O>O1CCOCC1>[CH:1]([N:5]([C:19]1[O:20][CH:21]=[C:17]([CH3:16])[N:18]=1)[C:6](=[O:10])[CH2:7][CH2:8][CH3:9])([CH2:3][CH3:4])[CH3:2]

Participants

Conditions

Temperature: 10 °C

Procedure

N-s-Butyl-butyramide (0.99 g, 0.0069 m) in dry dioxan (10 ml) was cooled to 10° 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 15 minutes at 10° C. and then 4-methyl-2-methylsulphinyloxazole (1.0 g, 0.0068 m) in dry dioxan (10 ml) was added and the mixture allowed to warm to room temperature. It was stirred for 3 hours and then hydrolysed with water. The solvent was removed in vacuo and the ether extract of the residue was chromatographed on silica using ether. The resulting compound (title product) was distilled in vacuo as a colourless oil 0.95 g, b.p. 75°-76° C./0.5 mm.

Workup

temperatureto warm to room temperature
stirringIt was stirred for 3 hours
customThe solvent was removed in vacuo
extractionthe ether extract of the residue
customwas chromatographed on silica
distillationThe resulting compound (title product) was distilled in vacuo as a colourless oil 0.95 g, b.p. 75°-76° C./0.5 mm

Sources & evidence

ORD record: ord-a18a9eefe37a4813b627d872e5a8ab35
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04143047

Reaction notes

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