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

HRID 1276608Notes

Reaction equation

HRID 1276608 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 81.3%

Reagents, catalysts & solvents 1

HCID 7997Propyl AcetateSolvent

Procedure

To a slurry of 2-amino-5-iodobenzoic acid (20 g, 0.076 mol) in n-propyl acetate (63 mL) was added triethylamine (11.6 mL, 0.0.84 mol) followed by n-propyl isothiocyanate (8.7 mL, 0.084 mol) at room temperature. The resulting solution was heated to reflux and the water generated was removed in a Dean Stark trap. After 4 h, the reaction mixture was cooled to room temperature and filtered. The wetcake was washed with fresh n-propyl acetate and dried at 60° C. under vacuum. In this manner, 21.4 g of the title compound was obtained as a light tan solid. See Step 1A for 1H NMR data, the UV spectrum matched that of the material made previously.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. customthe water generated was removed in a Dean Stark trap
  4. filtrationfiltered
  5. washThe wetcake was washed with fresh n-propyl acetate
  6. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-0cdeababcb1543e481609e311f8aad86
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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