Triethylamine → 2,3-Dihydro-6-iodo-3-propyl-2-thioxo-4(1H)-quinazolinone

HRID 1276607Notes

Reaction equation

HRID 1276607 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.C(N(CC)CC)C.[CH2:19]([N:22]=[C:23]=[S:24])[CH2:20][CH3:21]>C(OCCC)(=O)C>[I:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:23](=[S:24])[N:22]([CH2:19][CH2:20][CH3:21])[C:4]2=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69403Propyl IsothiocyanateHCID 72911Benzoic acid, 2-amino-5-iodo-

Product 1

HCID 108933552,3-Dihydro-6-iodo-3-propyl-2-thioxo-4(1H)-quinazolinoneYield 85.9%

Reagents, catalysts & solvents 1

HCID 7997Propyl AcetateSolvent

Procedure

To a slurry of 2-amino-5-iodobenzoic acid (100 g, 0.38 mol) in n-propyl acetate (315 mL) was added triethylamine (58 mL, 0.42 mol) at room temperature. The resulting solution was heated to reflux and n-propyl isothiocyanate (43 mL, 0.42 mol) was added over a one hour period. The reaction mixture was maintained at reflux for 18 h, then cooled to room temperature and filtered. The wetcake was washed with fresh propyl acetate and dried at 60° C. under vacuum. In this manner, 113 g of the title compound was obtained as a tan solid. m.p.>200° C.; 1H NMR (Me2SO--d6): δ13.02 (bs,1H), 8.22 (d,1H), 8.06 (dd,1H), 7.21 (d,1H), 4.34 (m,2H), 1.69 (m,2H), 0.93 (t,3H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was maintained
  4. temperatureat reflux for 18 h
  5. filtrationfiltered
  6. washThe wetcake was washed with fresh propyl acetate
  7. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-7fa1ff2483104a9584c08f248a340520
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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