Urea → 6-bromo-5-fluoroquinazolin-2(1H)-one

HRID 56477Notes

Reaction equation

HRID 56477 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[C:6]([F:10])[C:5]([Br:11])=[CH:4][CH:3]=1.[NH2:12][C:13](N)=[O:14]>>[Br:11][C:5]1[C:6]([F:10])=[C:7]2[C:2](=[CH:3][CH:4]=1)[N:1]=[C:13]([OH:14])[N:12]=[CH:8]2

Participants

3

Reactant 2

HCID 1176UreaHCID 593253016-Amino-3-bromo-2-fluorobenzaldehyde

Product 1

HCID 1785175476-bromo-5-fluoroquinazolin-2(1H)-oneYield 99%

Conditions

Temperature
180 °C

Procedure

A mixture of 6-amino-3-bromo-2-fluorobenzaldehyde (3.0 g, 13.76 mmol) and urea (12.40 g, 206.40 mmol) was heated to 180° C. and stirred for 2 hours. The reaction mixture was cooled to room temperature. The resulting precipitate was collected, washed with water (3×100 mL) and co-evaporated with toluene three times to completely remove the moisture trapped. The title compound (3.3 g, 99%) was obtained as a yellow solid. MS (ES+) C8H4BrFN2O requires: 242, found: 243, 245 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe resulting precipitate was collected
  3. washwashed with water (3×100 mL) and co-evaporated with toluene three times
  4. customto completely remove the moisture

Sources & evidence

ORD record
ord-3d8cf525cf674d158afa3669929b43d9
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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