Methylamine → 3-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dione

HRID 1199643Notes

Reaction equation

HRID 1199643 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=O)[O:4][C:2]2=[O:3].[CH3:13][NH2:14]>O1CCCC1>[CH3:13][N:14]1[C:2](=[O:3])[C:1]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 8359Isatoic Anhydride

Product 1

HCID 3443853-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6 g isatoic anhydride was stirred in 100 ml dry tetrahydrofurane (THF) and methylamine was passed through the mixture for 5 min. The resulting solution was evaporated and the residue was again dissolved in THF (100 ml) and charged with 15 ml 30% phosgene solution in toluene. The mixture was heated to reflux and additional 15 ml phosgene solution was added. After 4 hours reflux the mixture was cooled and evaporated to dryness. The residue was treated with water and the crystals were collected by filtration. The yield was 3.5 g. M.p. 240.4°-240.5° C.

Workup

  1. customThe resulting solution was evaporated
  2. dissolutionthe residue was again dissolved in THF (100 ml)
  3. additioncharged with 15 ml 30% phosgene solution in toluene
  4. temperatureThe mixture was heated
  5. temperatureto reflux
  6. additionadditional 15 ml phosgene solution was added
  7. temperatureAfter 4 hours reflux the mixture
  8. temperaturewas cooled
  9. customevaporated to dryness
  10. additionThe residue was treated with water
  11. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-4b80257ddb6c4129bbca2ef98d895b2d
Source dataset
uspto-grants-1990_02
Patent number
US04902686

Reaction notes

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