Ethyl 2-oxocyclohexanecarboxylate → HCID 135600044, compound

HRID 1714776Notes

Reaction equation

HRID 1714776 reaction equation
[Na].[N+:2]([NH:5][C:6]([NH2:8])=[NH:7])([O-:4])=[O:3].CC[O:11][C:12]([CH:14]1[C:19](=O)[CH2:18][CH2:17][CH2:16][CH2:15]1)=O>CO>[N+:2]([NH:5][C:6]1[NH:8][C:12](=[O:11])[C:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:7]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 5360545SodiumHCID 86287517Nitroguanidine

Product 1

HCID 135600044HCID 135600044, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 14 ml of methanol, 256 mg of sodium was added at room temperature under stirring, then 1.04 g of nitroguanidine was added, followed by 45 minutes' heating under reflux. Successively, 1.70 g of ethyl 2-cyclohexanonecarboxylate was added, followed by 9 hours' heating under reflux. After cooling the reaction mixture, the solvent was distilled off under reduced pressure. Water was added to the residue, and the system was acidified with acetic acid. The precipitate was recovered by filtration and dried to provide 1.76 g (84%) of 2-nitroamino-5,6,7,8-tetrahydro-3H-quinazolin-4-one.

Workup

  1. temperature' heating
  2. temperatureunder reflux
  3. waitfollowed by 9 hours
  4. temperature' heating
  5. temperatureunder reflux
  6. temperatureAfter cooling the reaction mixture
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionWater was added to the residue
  9. filtrationThe precipitate was recovered by filtration
  10. customdried

Sources & evidence

ORD record
ord-1551be0f1b754a419bd1ae2e9f3117cc
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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