Diethylamine → HCID 19735944, compound
Reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.[C:13]([O:16][CH2:17][C:18](Cl)=[O:19])(=[O:15])[CH3:14]>C(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH3:5])[C:18](=[O:19])[CH2:17][O:16][C:13](=[O:15])[CH3:14])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a 0° C. solution of diethylamine (1819 mL) and triethylamine (25.5 mL) in 500 mL of methylene chloride was added dropwise, with stirring, 25 g of acetoxyacetyl chloride. The ice bath was removed, and the mixture allowed to warm to 20° C. while stirring for an additional 2 hr. After filtration to remove amine hydrochloride salts, the methylene chloride solution was evaporated under reduced pressure to provide 29.1 g of crude, N,N-diethylacetoxyacetamide, as a yellow oil. The yellow oil was dissolved in 125 mL of methanol and 168 mL of 1N sodium hydroxide added with stirring. A slight exotherm was noted, and the mixture was allowed to stir for 2 hr. without further warming. Solvents were removed under reduced pressure to 1/4 volume, and the remaining aqueous solution extracted with ethyl acetate (200 ml). The ethyl acetate extract was dried over anh. sodium sulfate, and evaporated under reduced pressure to provide 14.0 g of N,N-diethylglycolamide as a yellow oil.
Workup
- customThe ice bath was removed
- stirringwhile stirring for an additional 2 hr
- filtrationAfter filtration
- customto remove amine hydrochloride salts
- customthe methylene chloride solution was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-3e5339d9f42349c4863c23595fc6ad1d
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05270331
Reaction notes
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