2,4,6-Trimethylbenzoic acid → 3-(2,4-Dichlorophenyl)-6-fluoroquinazoline-2,4(1H,3H)-dione

HRID 862893Notes

Reaction equation

HRID 862893 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[F:12][C:13]1[CH:22]=[C:17]([C:18](OC)=[O:19])[C:16]([NH2:23])=[CH:15][CH:14]=1.CC1C=C(C)C=C(C)C=1[C:27](O)=[O:28].CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18](=[O:19])[C:17]2[C:16](=[CH:15][CH:14]=[C:13]([F:12])[CH:22]=2)[NH:23][C:27]1=[O:28]

Participants

6

Reactant 4

HCID 101942,4,6-Trimethylbenzoic acidHCID 118992,4-DichloronitrobenzeneHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 2783401Methyl 2-amino-5-fluorobenzoate

Product 1

HCID 40212773-(2,4-Dichlorophenyl)-6-fluoroquinazoline-2,4(1H,3H)-dioneYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

17.2% by weight of 2,4-dichloronitrobenzene, 15.6% by weight of methyl 5-fluoroanthranilate, 1.5% by weight of Pd--C (5%), 1.0% by weight of 2,4,6-trimethylbenzoic acid and 0.4% by weight of 3,4,7,8-tetramethyl-1,10-phenanthroline are dissolved in 64.3% by weight of toluene and filled into an HC-4 autoclave. A pressure of 100 bar of CO is set and the temperature is increased to 180° C. After 2 hours, the autoclave is allowed to cool, and the product is filtered off together with the active carbon and recrystallized from dichlorobenzene. 51% of 3-(2,4-dichlorophenyl)-6-fluoro-2,4(1H,3H)-quinazolinedione is obtained.

Workup

  1. additionfilled into an HC-4 autoclave
  2. temperatureto cool
  3. filtrationthe product is filtered off together with the active carbon
  4. customrecrystallized from dichlorobenzene

Sources & evidence

ORD record
ord-1d181185c3ff4e46a39c42eee54d8537
Source dataset
uspto-grants-1998_02
Patent number
US05719284

Reaction notes

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