Benzoic acid, 2-amino-5-iodo- → 6-Iodoquinazolin-4-one

HRID 991463Notes

Reaction equation

HRID 991463 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(O)(=O)C.[CH:16](N)=[NH:17]>C(O)C>[I:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[CH:16][NH:17][C:4]2=[O:5]

Participants

4

Reactant 2

HCID 72911Benzoic acid, 2-amino-5-iodo-HCID 160693Formamidine acetate

Product 1

HCID 1354016666-Iodoquinazolin-4-oneYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-amino-5-iodobenzoic acid (26.3 g, 100 mmol) and formamidine acetate (13.5 g, 130 mmol) in ethanol (400 mL) was refluxed for 20 hours. After cooling to 0° C., the solid product was collected by filtration. Further drying in vacuo provided 6-iodo4-quinazolinone 12 (22.0 g, 81%) as a grey crystalline solid. 1H NMR (400 MHz; DMSO-d6) δ: 12.38 (br. s, 1H), 8.35 (d, 1H), 8.05-8.10 (m, 2H), 7.43 (dd, 1H). LRMS: 272.9 (MH+).

Workup

  1. filtrationthe solid product was collected by filtration
  2. customFurther drying in vacuo

Sources & evidence

ORD record
ord-f2060f2956a84075ba39b3e34cd71fc3
Source dataset
uspto-grants-2002_10
Patent number
US06465449B1

Reaction notes

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