Potassium Carbonate → HCID 178498350, compound

HRID 578711Notes

Reaction equation

HRID 578711 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[N:3]1.[I:16]N1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[I:16][C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=1)[NH:5][CH:4]=[N:3][C:2]2=[O:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120273N-Iodosuccinimide3×HCID 178497557HCID 178497557, compound

Product 1

HCID 178498350HCID 178498350, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of Methyl 4-oxo-1,4-dihydroquinazoline-8-carboxylate (6.0 g, 0.0294 mol) in sulphuric acid (48 mL) was added N-Iodosuccinimide (53 g, 0.2382 mol; 4 equiv of NIS was added at the beginning of reaction and the remaining NIS was added at day-2, day-3 and day-4 of the reaction in equal portions). The reaction mixture was stirred at 40° C. for 8 days and cooled to room temperature. (The completion of reaction was monitored by LCMS). The reaction mixture was carefully poured on-to ice cold solution of saturated potassium carbonate and maintained a basic pH. The precipitate was filtered, washed with water and dried. This solid was further suspended in saturated sodium bicarbonate (100 mL) containing methanol (20 mL). After stirring for 30 min, the insoluble solid was collected by filtration. This material was further slurred in a mixture of chloroform and methanol (1:1) and filtered and dried under vacuum to afford (5.5 g, 56%) of the title compound as an off white solid. TLC-: Chloroform/Methanol: (9/1): Rf=0.25. LCMS: Mass found (M+1, 331.0).

Workup

  1. customday-4 of the reaction in equal portions)
  2. temperaturecooled to room temperature
  3. custom(The completion of reaction
  4. temperaturemaintained a basic pH
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried
  8. additioncontaining methanol (20 mL)
  9. stirringAfter stirring for 30 min
  10. filtrationthe insoluble solid was collected by filtration
  11. additionThis material was further slurred in a mixture of chloroform and methanol (1:1)
  12. filtrationfiltered
  13. customdried under vacuum

Sources & evidence

ORD record
ord-efb279e53ae9478986a7d48cfc28978f
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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