Ethanol → HCID 21329557, compound

HRID 613945Notes

Reaction equation

HRID 613945 reaction equation
N#N.[CH3:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][C:6]=1[NH2:14].[CH2:15](O)[CH3:16]>>[CH3:3][N:4]1[C:5]2[CH:10]=[CH:9][C:8]([CH:11]([CH3:12])[CH3:13])=[CH:7][C:6]=2[N:14]=[C:15]1[CH3:16]

Participants

3

Reactant 2

HCID 702EthanolHCID 86736368HCID 86736368, compound

Product 1

HCID 21329557HCID 21329557, compound

Procedure

A mixture of 6.66 g. (0.041 mole) of N2 -methyl-5-isopropyl-1,2-phenylenediamine and 10.02 g. (0.081 mole) of ethyl methylcarboximidate hydrochloride in 100 ml. of absolute ethanol was stirred at room temperature for 40 hours and then refluxed for 18 hours. The reaction mixture was distilled to dryness under reduced pressure, 100 ml. of 4N HCl was added to the residue and then the mixture refluxed for 22 hours. After cooling, the resultant mixture was filtered and the filtrate added dropwise to 200 ml. of stirred ice and water containing 50 ml. of conc. ammonium hydroxide. The precipitated product was isolated by filtration, washed with water and then air-dried. The crude product was dissolved in 75 ml. of refluxing cyclohexane, filtered and the filtrate allowed to cool. The desired product crystallized from the cooled cyclohexane and was removed by filtration to give 2.73 g. (35.8%), melting at 130°-131° C.

Workup

  1. additionA mixture of 6.66 g
  2. temperaturerefluxed for 18 hours
  3. distillationThe reaction mixture was distilled to dryness under reduced pressure, 100 ml
  4. additionof 4N HCl was added to the residue
  5. temperaturethe mixture refluxed for 22 hours
  6. temperatureAfter cooling
  7. filtrationthe resultant mixture was filtered
  8. additionthe filtrate added dropwise to 200 ml
  9. customThe precipitated product was isolated by filtration
  10. washwashed with water
  11. customair-dried
  12. dissolutionThe crude product was dissolved in 75 ml
  13. filtrationof refluxing cyclohexane, filtered
  14. temperatureto cool
  15. customThe desired product crystallized from the cooled cyclohexane
  16. customwas removed by filtration
  17. customto give 2.73 g

Sources & evidence

ORD record
ord-c9edd32fe4304353a92e4956bce56296
Source dataset
uspto-grants-1979_03
Patent number
US04142886

Reaction notes

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