Diethylamine → HCID 86759153, compound

HRID 1166749Notes

Reaction equation

HRID 1166749 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[CH:14][C:15]([OH:17])=O)=[CH:5][CH:4]=1)=[O:2].[C:18](C1NC=CN=1)([C:20]1[NH:21][CH:22]=[CH:23]N=1)=O.C(NCC)C>CN(C=O)C.C(OC(=O)C)C>[C:15]([N:21]([CH2:22][CH3:23])[CH2:20][CH3:18])(=[O:17])[CH:14]=[CH2:13].[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)=[O:2]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 72514303HCID 72514303, compound

Product 1

HCID 86759153HCID 86759153, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-formylnaphthalene acrylic acid (210 mg, 0.92 mmol) in DMF (4 mL) was added carbonyl diimidazole (180 mg, 1.10 mmol). The mixture was stirred at room temperature for 1 hr, and diethylamine (0.1 mL, 71 mg, 0.97 mmol) was added. After stirring at room temperature for 16 hr, the mixture was diluted with ethylacetate (5 mL), extracted with water (5 mL), 1 N hydrochloric acid (5 mL), and water (3×5 mL), dried (MgSO4) and concentrated. After flash chromatography using hexane/ethylacetate 1:1, 115 mg (43%) of a yellow oil was obtained.

Workup

  1. stirringAfter stirring at room temperature for 16 hr
  2. extractionextracted with water (5 mL), 1 N hydrochloric acid (5 mL), and water (3×5 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69e6fb25f50a4f9a8398aa8f76c932be
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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