Dibutylamine → HCID 18944376, compound

HRID 400205Notes

Reaction equation

HRID 400205 reaction equation
[C:1]([OH:8])(=O)[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].C(N(CC)CC)C.ClC(OCC)=O.[CH2:22]([NH:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>CC(C)=O>[CH2:22]([N:26]([CH2:27][CH2:28][CH2:29][CH3:30])[C:1](=[O:8])[CH2:2][CH2:3][C:4](=[O:5])[CH3:6])[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 8148DibutylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 11579Levulinic Acid

Product 1

HCID 18944376HCID 18944376, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A! A solution of 100 g (0.86 mole) of levulinic acid in 1 l of acetone was added with 118 ml (0.86 mole) of triethylamine, and stirred for 15 minutes at room temperature. The mixture was cooled to 5° C. and added with a solution of ethyl chloroformate (83.3 ml, 0.86 mole) in 500 ml of acetone, then stirred for 15 minutes. The solid was filtered off and the mother liquor was added to a solution of dibutylamine (180 ml, 1 mole) in 1 l of acetone, then stirred overnight at room temperature, evaporated to dryness under vacuum, and the residue was dissolved in 1 l of ethyl ether, washed with 400 ml of 0.5N HCl, then with 400 ml of 0.5N sodium hydroxide. The ether phase was anhydrified over sodium sulfate and evaporated to dryness thus providing 175.5 g of a crude which by distillation under vacuum gave 112.5 g (yield: 57%) of N,N-dibutyl-4-oxo-pentanamide (b.p. 135°-138° C./1 mmHg).

Workup

  1. temperatureThe mixture was cooled to 5° C.
  2. stirringstirred for 15 minutes
  3. filtrationThe solid was filtered off
  4. stirringstirred overnight at room temperature
  5. customevaporated to dryness under vacuum
  6. dissolutionthe residue was dissolved in 1 l of ethyl ether
  7. washwashed with 400 ml of 0.5N HCl
  8. customevaporated to dryness
  9. customthus providing 175.5 g of a crude which
  10. distillationby distillation under vacuum

Sources & evidence

ORD record
ord-b6b5c32659c946b680856c1b77064d7a
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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