Formamide → 6-Chloro-8-iodo-4(3H)-quinazolinone

HRID 1049935Notes

Reaction equation

HRID 1049935 reaction equation
[CH:1]([NH2:3])=O.[NH2:4][C:5]1[C:13]([I:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:6]=1[C:7](O)=[O:8]>>[Cl:15][C:11]1[CH:10]=[C:6]2[C:5](=[C:13]([I:14])[CH:12]=1)[N:4]=[CH:1][NH:3][C:7]2=[O:8]

Participants

3

Reactant 2

HCID 713FormamideHCID 534416562-Amino-5-chloro-3-iodobenzoic acid

Product 1

HCID 1363443786-Chloro-8-iodo-4(3H)-quinazolinoneYield 84.5%

Conditions

Temperature
130 °C

Procedure

To a round bottom flask was added formamide (4 equiv., 13.5 mmol, 605 mg) and 2-amino-5-chloro-3-iodo-benzoic acid (1000 mg, 3.4 mmol). The reaction was capped and shaken at 130° C. for 72 h. The reaction was cooled to room temperature, then the precipitate was collected by filtration and washed 3× with water. The precipitate was dried under vacuum, yielding 881 mg of 6-chloro-8-iodo-3H-quinazolin-4-one as a purple solid. 1H NMR (400 MHz, DMSO) δ 12.66-12.49 (s, 1H), 8.40-8.37 (d, J=2.4 Hz, 1H), 8.24-8.21 (s, 1H), 8.09-8.05 (d, J=2.4 Hz, 1H). LCMS M/Z (M+H)=307.

Workup

  1. customThe reaction was capped
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe precipitate was collected by filtration
  4. washwashed 3× with water
  5. customThe precipitate was dried under vacuum

Sources & evidence

ORD record
ord-e3b463c5dc7446668b90dd56502b04b2
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

Loading…