Ethanol → 6-Iodo-3-propyl-1H-quinazoline-2,4-dione

HRID 1276618Notes

Reaction equation

HRID 1276618 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:15]=[C:16]=[O:17])[CH2:13][CH3:14].C(N(CC)CC)C.C(O)C>C(#N)C>[I:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:16](=[O:17])[N:15]([CH2:12][CH2:13][CH3:14])[C:4]2=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 61033Propyl isocyanate2×HCID 72911Benzoic acid, 2-amino-5-iodo-

Product 1

HCID 221165326-Iodo-3-propyl-1H-quinazoline-2,4-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.0 g (0.019 mol) 2-amino-5-iodobenzoic acid, 1.9 g (0.012 mol) n-propyl isocyanate, and 1.9 g (0.019 mol) triethylamine in 190 mL of acetonitrile was stirred at ambient temperature overnight. An additional 1.9 g (0.012 mol) of n-propyl isocyanate was added and stirring continued at ambient temperature for an additional 72 h. The reaction was then concentrated by atmospheric pressure distillation to deliver 7.8 g of an oil which solidified upon standing under reduced pressure. A 3.6 g portion of this crude material was subjected to heating neat at 190° C. for 0.75 h. The resulting reaction mass was cooled, treated with approximately 20 mL ethanol, agitated, and filtered. The filter cake was subsequently washed with ether and dried to deliver 1.8 g of the title compound, 1H NMR (300 MHz, Me2SO--d6): δ0.87 (s,3H); 1.50-1.69 (m,2H); 3.83 (t,2H); 6.99 (d,1H); 7.94 (dd,1H); 8.16 (d,1H); 11.50 (bs,1H).

Workup

  1. stirringstirring
  2. waitcontinued at ambient temperature for an additional 72 h
  3. concentrationThe reaction was then concentrated by atmospheric pressure distillation
  4. temperatureto heating neat at 190° C. for 0.75 h
  5. customThe resulting reaction mass
  6. temperaturewas cooled
  7. stirringagitated
  8. filtrationfiltered
  9. washThe filter cake was subsequently washed with ether
  10. customdried

Sources & evidence

ORD record
ord-6763b9f510b3417abc2b03f20857d625
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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