Urea → 7-(Trifluoromethyl)quinazoline-2,4(1H,3H)-dione

HRID 2400267Notes

Reaction equation

HRID 2400267 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:15][C:16](N)=[O:17]>O>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:15][C:16](=[O:17])[NH:1]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 678694-(Trifluoromethyl)anthranilic acid

Product 1

HCID 341761237-(Trifluoromethyl)quinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

2-Amino-4-trifluoromethylbenzoic acid (25.0 g, 122 mmol) and urea (75.0 g, 1.2 mol) were combined and heated at 200° C. while stirring. After 1 h, the reaction mixture was allowed to cool to 100° C. and water (100 mL) was added. The reaction mixture was then allowed to cool to room temperature and the solid was isolated by vacuum filtration washing with water (500 mL). The solid was then dried under vacuum (10 mbar, 50° C.). Yield=24 g, 86%; LC-MS: 2.1 min, 230 (M+); 1H NMR (DMSO-d6) δ 7.44 (s, 1 H) 7.47 (d, 1 H), 8.07 (d, 1 H), 11.43 (br s, 1 H), 11.56 (br s, 1 H).

Workup

  1. temperatureto cool to 100° C.
  2. temperatureto cool to room temperature
  3. customthe solid was isolated by vacuum filtration
  4. washwashing with water (500 mL)
  5. customThe solid was then dried under vacuum (10 mbar, 50° C.)
  6. custom2.1 min, 230 (M+)

Sources & evidence

ORD record
ord-007489fc28544b998eb52abcf1358457
Source dataset
uspto-grants-2014_08
Patent number
US08796180B2

Reaction notes

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