Phosgene → 2-Chloro-6-iodo-3-propyl-quinazolin-4-one

HRID 1276609Notes

Reaction equation

HRID 1276609 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[N:6]([CH2:13][CH2:14][CH3:15])[C:5]2=[O:16].C(Cl)([Cl:19])=O>C(OCCC)(=O)C>[Cl:19][C:7]1[N:6]([CH2:13][CH2:14][CH3:15])[C:5](=[O:16])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 108933556-iodo-3-propyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Product 1

HCID 108610142-Chloro-6-iodo-3-propyl-quinazolin-4-oneYield 101.4%

Reagents, catalysts & solvents 1

HCID 7997Propyl AcetateSolvent

Procedure

2,3-Dihydro-6-iodo-3-propyl-2-thioxo-4(1H)-quinazolinone (5 g, 0.014 mol) was slurried in n-propyl acetate and treated with phosgene (2.1 mL, 0.029 mol). The slurry was heated at reflux for 1 h. The excess phosgene was removed by co-distillation with n-propyl acetate at atmospheric pressure. The pot residue was then evaporated to dryness under vacuum. In this manner, 4.95 g of the title compound was obtained as a light pink solid. m.p. 98-100° C.; 1H NMR (Me2SO-d6): δ8.04 (d,1H), 8.16 (dd,1H), 7.31 (d,1H), 4.20 (m,2H), 1.78 (m,2H), 0.97 (t,3H).

Workup

  1. temperatureThe slurry was heated
  2. temperatureat reflux for 1 h
  3. customThe excess phosgene was removed by co-distillation with n-propyl acetate at atmospheric pressure
  4. customThe pot residue was then evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-94157694027b49d097bb0764d52a1b1b
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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