Ethylamine → HCID 56652978, compound

HRID 2410206Notes

Reaction equation

HRID 2410206 reaction equation
[CH:1]([C:5]1[CH:6]=[C:7](/[CH:19]=[CH:20]/[C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:8]=[C:9]2[C:14]=1[O:13][C:12](=[O:15])[C:11]([C:16](O)=[O:17])=[CH:10]2)([CH2:3][CH3:4])[CH3:2].S(Cl)(Cl)=O.[CH2:34]([NH2:36])[CH3:35]>C1(C)C=CC=CC=1>[CH:1]([C:5]1[CH:6]=[C:7](/[CH:19]=[CH:20]/[C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:8]=[C:9]2[C:14]=1[O:13][C:12](=[O:15])[C:11]([C:16]([NH:36][CH2:34][CH3:35])=[O:17])=[CH:10]2)([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 24386Thionyl ChlorideHCID 86692174HCID 86692174, compound

Product 1

HCID 56652978HCID 56652978, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of (E)-8-sec-butyl-2-oxo-6-(3-oxo-3-p-tolylprop-1-enyl)-2H-chromene-3-carboxylic acid of the formula (V) (0.5 g, 1.28 mmol) in toluene (15 mL), added thionyl chloride (1.0 mL), was refluxed for 3 h. The resulting solution was evaporated to dryness under reduced pressure, and the residue was dispersed in toluene (15 mL). The solvent was eliminated under reduced pressure. Dispersion in toluene and solvent elimination was repeated twice. The residue was dissolved toluene (10 mL) and added with stirring to a solution of the ethyl amine (0.06 g, 1.28 mmol). After 35 min at room temperature, the solvent was removed by evaporation under reduced pressure and extracted 3-fold with CHCl3 (20 mL). The combined organic layers were dried on Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue was chromatographed over silica gel (SiO2, 230-400 flash), eluting with a gradient of 20% ethyl acetate in hexane to 40% ethyl acetate in hexane, which upon concentration provides (E)-8-sec-butyl-N-ethyl-2-oxo-6-(3-oxo-3-p-tolylprop-1-enyl)-2H-chromene-3-carboxamide (General Formula VI). (0.34 g, 64% yield). White solid, m. p. 162-163° C.; 1H NMR (CDCl3 300 MHz): δ 8.93 (s, 1H), 7.96 (d, J=8.2 Hz, 2H), 7.83-7.76 (m, 3H), 7.54 (d, J=15.7 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H), 3.57-3.39 (m, 3H), 2.45 (s, 3H), 1.80-1.73 (m, 2H), 1.34 (d, J=6.9 Hz, 3H), 1.28 (t, J=7.3 Hz, 3H). 0.91 (t, J=7.3 Hz, 3H): 13C NMR (CDCl3, 75 MHz): δ 189.6, 161.2, 161.1, 153.1, 148.5, 144.1, 142.3, 136.5, 135.4, 132.2, 131.4, 128.8, 127.1, 123.2, 119.1, 119.0, 122.8, 34.9, 33.7, 29.8, 21.8, 20.6, 14.8, 12.1; ESI-MS (m/z): 418(M+H)+.

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe resulting solution was evaporated to dryness under reduced pressure
  3. additionthe residue was dispersed in toluene (15 mL)
  4. dissolutionThe residue was dissolved toluene (10 mL)
  5. additionadded
  6. customthe solvent was removed by evaporation under reduced pressure
  7. extractionextracted 3-fold with CHCl3 (20 mL)
  8. customThe combined organic layers were dried on Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe residue was chromatographed over silica gel (SiO2, 230-400 flash)
  12. washeluting with a gradient of 20% ethyl acetate in hexane to 40% ethyl acetate in hexane, which upon concentration

Sources & evidence

ORD record
ord-85dc0e16508a47e4becfa2343bc63cd8
Source dataset
uspto-grants-2014_08
Patent number
US08815940B2

Reaction notes

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