Ammonium Chloride → HCID 178469800, compound

HRID 1913516Notes

Reaction equation

HRID 1913516 reaction equation
C[N:2]([CH3:12])[CH:3]=[C:4]([N+:10]#[C-:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl-].[NH4+].[CH3:15][C@H:16]1[CH2:21][CH2:20][C@H](N)[CH2:18][CH2:17]1>>[CH3:15][C@H:16]1[CH2:21][CH2:20][C@H:12]([N:2]2[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:10]=[CH:11]2)[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 54355309Ethyl 3-(dimethylamino)-2-isocyanoacrylateHCID 178461305HCID 178461305, compound

Product 1

HCID 178469800HCID 178469800, compoundYield 89%

Conditions

Temperature
70 °C

Procedure

Ethyl 3-(dimethylamino)-2-isocyanoacrylate (Liebigs Annalen der Chemie, 1979, p. 1444) (1.52 g) was dissolved in trans-4-methylcyclohexylamine (3.07 g), and the solution was stirred at 70° C. for 4 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. This crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=2/1-1/2) to obtain the title compound (1.90 g).

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. customThis crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=2/1-1/2)

Sources & evidence

ORD record
ord-249359ebf551447a8c1e3a5f833bad3e
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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