Dimethylformamide diethylacetal → HCID 12747022, compound

HRID 437143Notes

Reaction equation

HRID 437143 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[C:6]([N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)=[N:7]2.C(O[CH:29](OCC)[N:30]([CH3:32])[CH3:31])C>O>[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([C:6]2[C:5]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[N:4][C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[N:1]=[CH:29][N:30]([CH3:32])[CH3:31])[N:7]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 12676683HCID 12676683, compound

Product 1

HCID 12747022HCID 12747022, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A 2.4 g. portion of 5-amino-2,3-bis(4-methyl-1-piperazinyl)quinoxaline prepared as in Example 3 is combined with 23.0 g. of dimethylformamide diethylacetal in a reaction flask. The suspension is heated in an oil bath at 135° C. with magnetic stirring. The solid is dissolved within four minutes and refluxing is continued for two hours. The reaction solution is cooled and stripped of solvent by water pump evacuation. The residual yellow solid is recrystallized by boiling in 200 ml. of hexane, after filtering to remove a small amount of insoluble material. The recrystallized material is collected by filtration and dried in vacuo over phosphorous pentoxide at 78° C. The above filtrate is set aside and the dried material is again recrystallized from 200 ml. of hexane in exactly the same manner as above, collected and dried to give 0.35 g. of orange solid. A yellowish-brown insoluble material removed by filtering the hot hexane prior to cooling is set aside. The final hexane cold filtrate and the initial hexane cold filtrate previously set aside are combined and the hexane is removed by water pump evacuation. The insoluble residue set aside previously is added to the combined filtrate residue and this is recrystallized from 70 ml. of hot acetonitrile by cooling at -10° C. The solid formed is collected by filtration, washed with cold acetonitrile and dried in vacuo over phosphorous pentoxide at 78° C. to give 1.6 g. of additional orange solid. The combined yield of the product of the example is 1.9 g., m.p. 183°-186° C.

Workup

  1. dissolutionThe solid is dissolved within four minutes
  2. temperaturerefluxing
  3. temperatureThe reaction solution is cooled
  4. customThe residual yellow solid is recrystallized
  5. filtrationof hexane, after filtering
  6. customto remove a small amount of insoluble material
  7. filtrationThe recrystallized material is collected by filtration
  8. dry with materialdried in vacuo over phosphorous pentoxide at 78° C
  9. customthe dried material is again recrystallized from 200 ml
  10. customof hexane in exactly the same manner as above, collected
  11. customdried
  12. customto give 0.35 g
  13. customA yellowish-brown insoluble material removed
  14. filtrationby filtering the hot hexane
  15. temperatureto cooling
  16. customthe hexane is removed by water pump evacuation
  17. additionThe insoluble residue set aside previously is added to the combined filtrate residue
  18. customthis is recrystallized from 70 ml
  19. temperatureof hot acetonitrile by cooling at -10° C
  20. customThe solid formed
  21. filtrationis collected by filtration
  22. washwashed with cold acetonitrile
  23. dry with materialdried in vacuo over phosphorous pentoxide at 78° C.
  24. customto give 1.6 g

Sources & evidence

ORD record
ord-670d9d36766e403db7eeca6c964b0a17
Source dataset
uspto-grants-1977_06
Patent number
US04029788

Reaction notes

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