Dibutylamine → HCID 19003310, compound

HRID 1654564Notes

Reaction equation

HRID 1654564 reaction equation
Cl.[CH3:2][C:3]1([CH3:25])[CH2:8][CH:7]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][C:16]([C:19](Cl)=[O:20])=[CH:17][CH:18]=[C:11]3[C:10]2=[O:22])[CH2:6][C:5]([CH3:24])([CH3:23])[NH:4]1.[CH2:26]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH3:29].C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl.O.CN(C)C=O>[CH3:2][C:3]1([CH3:25])[CH2:8][CH:7]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][C:16]([C:19]([N:30]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:26][CH2:27][CH2:28][CH3:29])=[O:20])=[CH:17][CH:18]=[C:11]3[C:10]2=[O:22])[CH2:6][C:5]([CH3:24])([CH3:23])[NH:4]1

Participants

8

Reactant 4

HCID 8148DibutylamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 131718103HCID 131718103, compound

Product 1

HCID 19003310HCID 19003310, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed 5.0 g (0.013 mol) of acid chloride of Example 2 and 50 ml of 2% dimethylformamide in methylene chloride. This mixture was stirred during the addition of 1.7 g (0.013 mol) of di-n-butylamine accompanied by a 10° C. exotherm. The reaction mixture was cooled to ambient temperature and 2.8 g (0.028 mol) triethylamine were added, producing an exotherm of about 10° C. The reaction was cooled to room temperature and allowed to stir for 1 hour, then transferred to a separatory funnel with 50 ml methylene chloride and 50 ml water. Upon shaking, an emulsion formed which was broken by the addition of 25 ml of 5% sodium hydroxide. The phases were separated and the organic phase was further extracted with three 50 ml portions of 5% sodium hydroxide and three 50 ml portions of water. The organic solution was dried with anhydrous magnesium sulfate and the solvent stripped using aspirator and high vacuum systems. The product was 5.0 g of a yellow liquid. The infrared spectrum (between salt plates) showed two carbonyl absorptions at 1718 cm-1 (imide) and 1642 cm-1 (amide). The NMR spectrum showed the anticipated aromatic ring (7.5-8.0 ppm, multiplet, 3H), the amide methylene hydrogens (2.9-3.8 ppm, broad doublet, 4H) and the HALS group [4.4-4.9 ppm, multiplet, 1H; 0.5-2.3 ppm, several multiplets including two singlets (1.2 and 1.3 ppm)].

Workup

  1. customInto a 125 ml reaction flask
  2. customequipped with a magnetic stirrer
  3. customthermometer, condenser and nitrogen atmosphere were placed
  4. customaccompanied by a 10° C.
  5. customproducing an exotherm of about 10° C
  6. temperatureThe reaction was cooled to room temperature
  7. stirringUpon shaking
  8. customan emulsion formed which
  9. customThe phases were separated
  10. extractionthe organic phase was further extracted with three 50 ml portions of 5% sodium hydroxide and three 50 ml portions of water
  11. dry with materialThe organic solution was dried with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-693f6300b884402b9af331c9640d3384
Source dataset
uspto-grants-1995_04
Patent number
US05408008

Reaction notes

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