Dimethylformamide dimethyl acetal → HCID 12747028, compound

HRID 437144Notes

Reaction equation

HRID 437144 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]1)[C:6]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:22]1)=[N:5]2.CO[CH:32](OC)[N:33]([CH3:35])[CH3:34]>>[CH2:18]([N:15]1[CH2:16][CH2:17][N:12]([C:7]2[C:6]([N:21]3[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][CH3:29])[CH2:25][CH2:26]3)=[N:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([N:1]=[CH:32][N:33]([CH3:35])[CH3:34])[CH:3]=3)[N:8]=2)[CH2:13][CH2:14]1)[CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 12747025HCID 12747025, compound

Product 1

HCID 12747028HCID 12747028, compound

Conditions

Temperature
64 °C

Procedure

A 6.0 g. portion of 6-amino-2,3-bis(4-propyl-1-piperazinyl)quinoxaline (prepared as in Example 5) is mixed with 3.42 ml. of dimethylformamide dimethylacetal in a reaction flask fitted with a reflux condenser. The mixture is refluxed in an oil bath at 64° C. for three hours. The condenser is removed and the distillate is allowed to boil off as the oil bath is permitted to cool overnight. The flask is stripped of solvent by water pump evacuation and the residue is dissolved in 50 ml. of acetonitrile; is treated with activated charcoal and filtered. The filtrate is cooled at -10° C. causing separation of an oil. The supernatant is decanted and the oil is air dried to yield a crystalline solid which is recrystallized from 20 ml. of hexane by cooling at -10° C. The precipitate is filtered and is air dried to give the product of the example as a yellow solid, m.p. 95.5°-98° C.

Workup

  1. customThe condenser is removed
  2. temperatureto cool overnight
  3. dissolutionthe residue is dissolved in 50 ml
  4. additionis treated with activated charcoal
  5. filtrationfiltered
  6. temperatureThe filtrate is cooled at -10° C.
  7. customseparation of an oil
  8. customThe supernatant is decanted
  9. customdried
  10. customto yield a crystalline solid which
  11. customis recrystallized from 20 ml
  12. temperatureof hexane by cooling at -10° C
  13. filtrationThe precipitate is filtered
  14. customdried
  15. customto give the product of the example as a yellow solid, m.p. 95.5°-98° C.

Sources & evidence

ORD record
ord-d362158291214058bb31dafc144d60be
Source dataset
uspto-grants-1977_06
Patent number
US04029788

Reaction notes

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