Ethanol → HCID 15894616, compound

HRID 1857938Notes

Reaction equation

HRID 1857938 reaction equation
C(O)C.[C:4]([C:12]1[CH:13]=[C:14]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]1[C:16]([CH:17]=[CH:18][CH:19]=[C:20]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N+:15]2[O-])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.OS([O-])(=O)=O.[Na+]>O>[C:4]([C:12]1[CH:13]=[C:14]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]1[C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:19][CH:18]=[CH:17][C:16]=1[NH:15]2)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 516919Sodium BisulfateHCID 15894615HCID 15894615, compound

Product 1

HCID 15894616HCID 15894616, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a boiled ethanol solution (300 mL) of 7-benzoyl-1-ethoxycarbonylphenazine 5-oxide (4.00 g, 10.7 mmol. obtained in Reference Example 1) was dropwise added for a period of one hour an aqueous solution (150 mL) of 85% sodium hydrosulfate (8.86 g, 43.2 mol.) in gaseous nitrogen atmosphere. After the dropwise addition was complete, the reaction mixture was further heated under reflux for 10 minutes. The refluxed mixture was then cooled to room temperature. To the cooled mixture was added water (150 mL). Thus deposited crystalline product was collected by filtration and washed with water. The washed product was placed under reduced pressure at 40° C. for 16 hours in the presence of diphosphorus pentoxide to dryness. Thus, 3.10 g (81%) of the desired compound was obtained as a brown-violet crystalline product. mp: 175-177° C.

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe reaction mixture was further heated
  3. temperatureunder reflux for 10 minutes
  4. filtrationThus deposited crystalline product was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-fd714a31ba1641cebe1cbb95fb5e45a9
Source dataset
uspto-grants-2000_11
Patent number
US06150363

Reaction notes

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