4-Methylmorpholine → N-n-Hexyl-N-methyl-5-acetylfuran-2-carboxamide

HRID 1194320Notes

Reaction equation

[C:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC)=O.[CH2:25]([NH:31][CH3:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>ClCCl>[CH2:25]([N:31]([CH3:32])[C:9]([C:7]1[O:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1)=[O:11])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: -20 °C

Procedure

To a stirred slurry of 4.6 g. (0.03 mole) of 5-acetylfuran-2-carboxylic acid in 150 ml. of dichloromethane was added 3.3 g. (0.033 mole) of N-methylmorpholine. The resulting solution was cooled to -20° C., and 3.6 g. (0.033 mole) of ethyl chloroformate was added dropwise, with stirring. Stirring was continued for 1 hour at -15° C. and then 3.8 g. (0.033 mole) of n-hexylmethylamine was added dropwise at -20° C. The resulting mixture was stirred for 1.5 hours while being allowed to warm to room temperature. The reaction mixture was then washed with water, dried (Na2SO4) and evaporated in vacuo to give 7.5 g. of an oil. This oil was chromatographed on silica gel, eluting with 1:1 hexane-ethyl acetate, to give 5.6 g. of the title amide as an oil.

Workup

stirringStirring
stirringThe resulting mixture was stirred for 1.5 hours
temperatureto warm to room temperature
washThe reaction mixture was then washed with water
dry with materialdried (Na2SO4)
customevaporated in vacuo
customto give 7.5 g
customThis oil was chromatographed on silica gel
washeluting with 1:1 hexane-ethyl acetate
customto give 5.6 g

Sources & evidence

ORD record: ord-13cc75cac62646c7a5c56b091f52a63e
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04814341

Reaction notes

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