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

HRID 1917783Notes

Reaction equation

HRID 1917783 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)(=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 99.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-amino-5-iodobenzoic acid (9.00 g, 34.2 mmol) and formamidine acetate (18.00 g, 173 mmol) in acetic acid (50 mL) was heated at 130° C. for 3 hours. After it was cooled down to room temperature, it was quenched with water, filtered, washed with water, and dried under vacuum with P2O5 to afford 6-iodoquinazolin-4(3H)-one as solid (9.289 g, 99.8%). 1H NMR (300 MHz, DMSO-d6) δ 8.38 (d, 1H), 8.13 (s, 1H), 8.09 (dd, 1H), 7.46 (d, 1H); LC-MS (ESI) m/z 273 (M+H)+.

Workup

  1. temperatureAfter it was cooled down to room temperature
  2. customit was quenched with water
  3. filtrationfiltered
  4. washwashed with water
  5. dry with materialdried under vacuum with P2O5

Sources & evidence

ORD record
ord-b95f00be0fda415e920d576a8bea199d
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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