Nitric Acid → HCID 54433626, compound

HRID 1283475Notes

Reaction equation

HRID 1283475 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[N:7]=[C:6]([N:16]2[CH2:21][CH2:20][S:19][CH2:18][CH2:17]2)[CH:5]=1)[CH3:2].S(=O)(=O)(O)[OH:23].[N+:27]([O-])([OH:29])=[O:28]>>[CH2:1]([O:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[N:7]=[C:6]([N:16]2[CH2:17][CH2:18][S:19](=[O:23])[CH2:20][CH2:21]2)[C:5]=1[N+:27]([O-:29])=[O:28])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 21517815HCID 21517815, compound

Product 1

HCID 54433626HCID 54433626, compound

Conditions

Temperature
0 °C

Procedure

1 gm of 6-ethoxy- 2-piperazino-4-thiomorpholino-pyrimidine was added to 3 ml of concentrated sulfuric acid, whereby the temperature of the resulting suspension rose to 50°C. After cooling to 0°C, 2 ml of concentrated nitric acid were added dropwise while stirring. After stirring it for another hour at room temperature, the reaction mixture was filtered through glass wool, and the filtrate was stirred into ice water. By careful addition of aqueous 40% sodium hydroxide, the mixture was adjusted to pH 9 and extracted with chloroform. The chloroform phase was washed with water, dried with sodium sulfate, and the solvent was distilled off in vacuo. The residue was recrystallized from ethanol. Yield: 0.8 gm (66.9% of theory); m.p. 223°-224°C.

Workup

  1. customrose to 50°C
  2. stirringAfter stirring it for another hour at room temperature
  3. filtrationthe reaction mixture was filtered through glass wool
  4. stirringthe filtrate was stirred into ice water
  5. additionBy careful addition of aqueous 40% sodium hydroxide
  6. extractionextracted with chloroform
  7. washThe chloroform phase was washed with water
  8. dry with materialdried with sodium sulfate
  9. distillationthe solvent was distilled off in vacuo
  10. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a880b2f880554ebf9f0ae61a21c16126
Source dataset
uspto-grants-1976_08
Patent number
US03975384

Reaction notes

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