Ammonium Chloride → HCID 68248305, compound

HRID 1913519Notes

Reaction equation

HRID 1913519 reaction equation
C[N:2]([CH3:12])[CH:3]=[C:4]([N+:10]#[C-:11])[C:5]([O:7]CC)=O.[Cl-].[NH4+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:21]([CH:23]1[CH2:28][CH2:27]C(N)[CH2:25][CH2:24]1)[CH3:22]>O1CCCC1.C(OCC)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>[CH2:21]([CH:23]1[CH2:28][CH2:27][CH:12]([N:2]2[CH:3]=[C:4]([CH2:5][OH:7])[N:10]=[CH:11]2)[CH2:25][CH2:24]1)[CH3:22]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 4208194-Ethylcyclohexan-1-amineHCID 21226445Aluminium lithium hydrideHCID 54355309Ethyl 3-(dimethylamino)-2-isocyanoacrylate

Product 1

HCID 68248305HCID 68248305, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 24436Sodium SulfateSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 3-(dimethylamino)-2-isocyanoacrylate (2.00 g) was dissolved in 4-ethylcyclohexylamine (3.37 g), and the solution was stirred at 70° C. for 4.5 hours. To the reaction solution, saturated aqueous ammonium chloride was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. Lithium aluminum hydride (92%, 0.490 g) was suspended in tetrahydrofuran (12 mL). The produced crude product was dissolved in tetrahydrofuran (12 mL), and this solution was slowly added dropwise to the suspension at 0° C. After stirring at 0° C. for 30 minutes, the reaction solution was diluted with diethyl ether, and saturated aqueous sodium sulfate was added thereto. After stirring at room temperature for 1 hour, the formed inorganic salt was removed by filtration through celite. The filtrate was concentrated under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: methylene chloride-methylene chloride/methanol=9/1) to obtain the title compound (1.35 g, diastereomeric mixture, trans:cis=4:1).

Workup

  1. extractionorganic matter was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain a crude product
  6. customThe produced crude product
  7. additionthis solution was slowly added dropwise to the suspension at 0° C
  8. stirringAfter stirring at 0° C. for 30 minutes
  9. additionwas added
  10. stirringAfter stirring at room temperature for 1 hour
  11. customthe formed inorganic salt was removed by filtration through celite
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. customto obtain a crude product
  14. customThis crude product was purified by silica gel column chromatography (eluting solvent: methylene chloride-methylene chloride/methanol=9/1)

Sources & evidence

ORD record
ord-32d5cd479b1840fa8d862db573e6a393
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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