Diethyl Ether → HCID 12818620, compound

HRID 1703127Notes

Reaction equation

HRID 1703127 reaction equation
[CH:1]1([NH:7][C:8]2[N:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([CH:18]([C:22](Cl)=[O:23])[C:19](Cl)=[O:20])C.[CH2:25]([O:27]CC)[CH3:26]>>[CH2:25]([O:27][C:22]([C:18]1[C:19](=[O:20])[N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:8]2[C:9]([C:10]=1[NH2:11])=[CH:12][CH:13]=[CH:14][N:15]=2)=[O:23])[CH3:26]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 109209242-Ethylpropanedioyl dichlorideHCID 128186532-(Cyclohexylamino)pyridine-3-carbonitrile

Product 1

HCID 12818620HCID 12818620, compound

Procedure

To a solution of 20.1 g. (0.1 mole) of 2-cyclohexylaminonicotinonitrile in 1000 ml. of anhydrous ethyl ether was added 7.5 g. (0.05 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 1 hour. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was triturated with 30 ml. of ether and was filtered. The filtrate was evaporated and this residue was added to a solution of 2.3 g. (0.1 g. atom) of sodium in 250 ml. of ethanol. The mixture was stirred at room temperature for 5 minutes, diluted with water and was acidified with conc. hydrochloric acid. The solution was cooled in ice and the precipitate which formed was collected, air dried and was recrystallized twice from ethyl acetate to afford 1.0 g. of the title product, m.p. 172°-175° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in a rotary evaporator
  3. customThe residue was triturated with 30 ml
  4. filtrationof ether and was filtered
  5. customThe filtrate was evaporated
  6. additionthis residue was added to a solution of 2.3 g
  7. stirringThe mixture was stirred at room temperature for 5 minutes
  8. additiondiluted with water
  9. temperatureThe solution was cooled in ice
  10. customthe precipitate which formed
  11. customwas collected
  12. customair dried
  13. customwas recrystallized twice from ethyl acetate
  14. customto afford 1.0 g

Sources & evidence

ORD record
ord-63c2efb02a844bcdab76c995f33bc583
Source dataset
uspto-grants-1982_09
Patent number
US04350817

Reaction notes

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