Hydrochloric Acid → HCID 576570, compound

HRID 1077249Notes

Reaction equation

HRID 1077249 reaction equation
[C:1]([CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][NH:20][C:21]([NH2:23])=[O:22]>C(O)(=O)C>[CH3:19][N:20]1[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:23][C:21]1=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8433DibenzoylmethaneHCID 11719Methylurea

Product 1

HCID 576570HCID 576570, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 15 g. of dibenzoylmethane and 43.5 g. of M-methylurea in 250 ml. of glacial acetic acid is refluxed for 8 hours while dry hydrogen chloride gas is bubbled through the reaction mixture. An additional amount of 5 equivalents of N-methylurea is then added and refluxing continued for another 8 hours while bubbling hydrogen chloride through the reaction system. The N-methylurea addition is again repeated and refluxing procedure continued for a further 8 hours. The resulting mixture is filtered and the filtrate evaporated in vacuo to dryness. The residue is taken up with methylene chloride, treated with 2N. sodium hydroxide and the methylene chloride layer separated. The aqueous layer is extracted three times with methylene chloride. All methylene chloride fractions are combined and extracted several times with water, dried, filtered and evaporated in vacuo to dryness. The residue is crystallized from methylene chloride/diethyl ether to obtain 1-methyl-4,6-diphenylpyrimidin-2(1H)-one, m.p. 183°-185°C.

Workup

  1. customis bubbled through the reaction mixture
  2. temperaturerefluxing
  3. customwhile bubbling hydrogen chloride through the reaction system
  4. additionThe N-methylurea addition
  5. temperaturerefluxing procedure
  6. waitcontinued for a further 8 hours
  7. filtrationThe resulting mixture is filtered
  8. customthe filtrate evaporated in vacuo to dryness
  9. additiontreated with 2N
  10. customsodium hydroxide and the methylene chloride layer separated
  11. extractionThe aqueous layer is extracted three times with methylene chloride
  12. extractionextracted several times with water
  13. customdried
  14. filtrationfiltered
  15. customevaporated in vacuo to dryness
  16. customThe residue is crystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-800e9e0ac95f42c7b31585e4c0e7509b
Source dataset
uspto-grants-1976_05
Patent number
US03959471

Reaction notes

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