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

HRID 1735968Notes

Reaction equation

HRID 1735968 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[F:12][C:13]1[CH:23]=[C:17]([C:18](OCC)=[O:19])[C:16]([NH2:24])=[CH:15][CH:14]=1.C[O-].[Na+]>CCCCCC>[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:23]=2)[NH:24][C:10]1=[O:11]

Participants

5

Reactant 3

HCID 757892,4-Dichlorophenyl isocyanateHCID 10942334Sodium MethoxideHCID 11126923Ethyl 2-amino-5-fluorobenzoate

Product 1

HCID 40212773-(2,4-Dichlorophenyl)-6-fluoroquinazoline-2,4(1H,3H)-dioneYield 96%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2,4-dichlorophenyl isocyanate (18.8 g, 0.10 mol) is introduced in portions at room temperature into a solution of ethyl 5-fluoroanthranilate (18.3 g, 0.10 mol) in hexane (120 ml). After addition is complete, the mixture is stirred under reflux for 2 hours. 3.60 ml of a 30% strength solution of methanolic sodium methoxide (0.020 mol) are metered in and the mixture is stirred under reflux for a further 2 hours, ethanol and methanol being distilled off. After cooling, the product is filtered off with suction and washed with 3×15 ml of hexane. The hexane-moist precipitate is treated with dilute hydrochloric acid and the residual hexane is removed by azeotropic distillation. The product is then filtered off with suction, washed with water and dried. 31.2 g of 3-(2,4-dichlorophenyl)-6-fluoro-2,4(1H,3H) -quinazolinedione (yield: 96.0% of theory) of melting point 312° to 314° C. are obtained.

Workup

  1. additionAfter addition
  2. temperatureunder reflux for 2 hours
  3. stirringis stirred
  4. temperatureunder reflux for a further 2 hours
  5. distillationethanol and methanol being distilled off
  6. temperatureAfter cooling
  7. filtrationthe product is filtered off with suction
  8. washwashed with 3×15 ml of hexane
  9. additionThe hexane-moist precipitate is treated with dilute hydrochloric acid
  10. customthe residual hexane is removed by azeotropic distillation
  11. filtrationThe product is then filtered off with suction
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-8db9a24ff1be46bb86e3f6824147c8ce
Source dataset
uspto-grants-1996_07
Patent number
US05539114

Reaction notes

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