Urea → HCID 178517410, compound

HRID 524034Notes

Reaction equation

HRID 524034 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH:4]=O.[NH2:11][C:12](N)=[O:13]>>[Br:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[N:1]=[C:12]([OH:13])[N:11]=[CH:4]2

Participants

3

Reactant 2

HCID 1176UreaHCID 235104752-Amino-5-bromobenzaldehyde

Product 1

HCID 178517410HCID 178517410, compoundYield 89%

Conditions

Temperature
180 °C

Procedure

A mixture of 2-amino-5-bromobenzaldehyde (29) (6 g, 30.0 mmol) and urea (30) (27 g, 450.0 mmol) was heated to 180° C. and stirred for 5 hours. LCMS showed the reaction was completed. The reaction mixture was cooled to room temperature, and the resulting precipitate was washed with H2O (3×500 mL) and co-evaporated with toluene three times to completely remove the moisture trapped. 6-bromoquinazolin-2-ol (31)(6 g, 89%) was obtained as a yellow solid. MS (ES+) C8H5BrN2O requires: 224. found: 225, 227 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washthe resulting precipitate was washed with H2O (3×500 mL) and co-evaporated with toluene three times
  3. customto completely remove the moisture

Sources & evidence

ORD record
ord-032a2f4676cc4437b460e744b76c102b
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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