N,N,N',N'-Tetramethylethylenediamine → N-(Butan-2-yl)-2-methyl-N-(4-methyl-1,3-oxazol-2-yl)propanamide

HRID 613994Notes

Reaction equation

[CH:1]([NH:5][C:6](=[O:10])[CH:7]([CH3:9])[CH3:8])([CH2:3][CH3:4])[CH3:2].CN(C)CCN(C)C.[H-].[K+].C(S([C:27]1[O:28][CH:29]=[C:30]([CH3:32])[N:31]=1)=O)CCC>S1(CCCC1)(=O)=O.O>[CH:1]([N:5]([C:27]1[O:28][CH:29]=[C:30]([CH3:32])[N:31]=1)[C:6](=[O:10])[CH:7]([CH3:9])[CH3:8])([CH2:3][CH3:4])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

N-s-Butyl-isobutyramide (2.30 g, 0.016 m) and tetramethylethylenediamine (1.87 g, 0.016 m) were stirred at 40° C. in sulpholane (20 ml) under nitrogen during the portionwise addition of a 50% potassium hydride/oil dispersion (1.29 g, 0.016 m). After the addition, the mixture was warmed to 70° C. and 2-n-butylsulphinyl-4-methyloxazole (3.0 g, 0.016 m) in sulpholane (20 ml) was added. The mixture was stirred at 70° C. for 6 hours and then hydrolysed with water. Removal of the solvent in vacuo and column chromatography on silica using diethyl ether gave the title compound, which was a colourless oil after distillation in vacuo, b.p. 82° C./0.8 mm.

Workup

additionAfter the addition
customRemoval of the solvent in vacuo and column chromatography on silica

Sources & evidence

ORD record: ord-809ad7da16ec41729497571ec64705bc
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04143047

Reaction notes

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