O-Xylene → 2-Amino-5,6,7,8-tetrahydroquinazolin-4(1H)-one

HRID 1732085Notes

Reaction equation

HRID 1732085 reaction equation
[C:1](=[O:4])(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[C:9]1(C)[C:10](C)=[CH:11][CH:12]=[CH:13][CH:14]=1>>[NH2:7][C:6]1[NH:8][C:1](=[O:4])[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[N:5]=1

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 1355047432-Amino-5,6,7,8-tetrahydroquinazolin-4(1H)-one

Procedure

A mixture of ethyl-2-cyclohexanone carboxylate (2.0 g) and guanidine carbonate (2.66 g) in xylene (40 ml) was refluxed overnight; after cooling the solid was collected by filtration, washed with water, methanol, and dried over MgSO4. 0.6 g of a white solid having a m.p. >300° C. was recovered. The solid was dissolved in Con. HCl, and excess HCl was removed in vacuo to dryness. The gummy residue was treated with methanol-ether to afford a colorless plate (0.6 g).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureafter cooling the solid
  3. filtrationwas collected by filtration
  4. washwashed with water, methanol
  5. dry with materialdried over MgSO4
  6. customwas recovered
  7. dissolutionThe solid was dissolved in Con
  8. customHCl, and excess HCl was removed in vacuo to dryness
  9. additionThe gummy residue was treated with methanol-ether
  10. customto afford a colorless plate (0.6 g)

Sources & evidence

ORD record
ord-16ad37063c564a518ae191396eb13bea
Source dataset
uspto-grants-1986_11
Patent number
US04625026

Reaction notes

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