Ammonium Chloride → HCID 178455353, compound

HRID 1913524Notes

Reaction equation

HRID 1913524 reaction equation
C[N:2]([CH3:12])[CH:3]=[C:4]([N+:10]#[C-:11])[C:5]([O:7]CC)=O.[Si:13]([O:20][C@H:21]1[CH2:26][CH2:25][C@H](N)[CH2:23][CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[Cl-].[NH4+]>O1CCCC1.C(OCC)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>[Si:13]([O:20][C@H:21]1[CH2:26][CH2:25][C@H:12]([N:2]2[CH:3]=[C:4]([CH2:5][OH:7])[N:10]=[CH:11]2)[CH2:23][CH2:22]1)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 54355309Ethyl 3-(dimethylamino)-2-isocyanoacrylateHCID 178455364HCID 178455364, compound

Product 1

HCID 178455353HCID 178455353, compoundYield 46.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 24436Sodium SulfateSolvent

Conditions

Temperature
85 °C

Procedure

Ethyl 3-(dimethylamino)-2-isocyanoacrylate (300 mg) and trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexylamine (Synthetic Communications, 1990, Vol. 20, p. 1073) (1.02 g) were mixed and stirred at 85° C. for 12 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. The residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate-4/1-1/1). Lithium aluminum hydride (92%, 105 mg) was suspended in tetrahydrofuran (8 mL). The produced crude product was dissolved in tetrahydrofuran (6 mL), and this solution was slowly added dropwise to the suspension at 0° C. After stirring at 0° C. for 1 hour, 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 washed with a mixed solvent of hexane and ethyl acetate (2:1) to obtain the title compound (260 mg).

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. customThe residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate-4/1-1/1)
  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 1 hour
  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. washThis crude product was washed with a mixed solvent of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8b944518dbb3498d9b6aebdc72ed1ad7
Source dataset
uspto-grants-2013_12
Patent number
US08609710B2

Reaction notes

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