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

HRID 1735967Notes

Reaction equation

HRID 1735967 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+]>CC(C)=O>[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 97.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of 2,4-dichlorophenyl isocyanate (18.8 g, 0.10 mol) in acetone (50 ml) is metered at room temperature into a solution of ethyl 5-fluoroanthranilate (18.3 g, 0.10 mol) in acetone (70 ml). After addition is complete the mixture is stirred at 90° C. for 2.5 hours. 1.80 ml of a 30% strength solution of methanolic sodium methoxide (0.010 mol) are metered in and the mixture is stirred under reflux for a further 2 hours. After cooling, the product is filtered off with suction and washed with 3×15 ml of acetone. The acetone-moist precipitate is treated with dilute hydrochloric acid and the residual acetone is removed by azeotropic distillation. The product is then filtered off with suction, washed with water and dried. 31.7 g of 3-(2,4-dichlorophenyl)-6-fluoro-2,4(1H,3H)-quinazolinedione (yield: 97.5% of theory) of melting point 313° to 314° C. are obtained.

Workup

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

Sources & evidence

ORD record
ord-75d516541d77403a8c767c83673423dd
Source dataset
uspto-grants-1996_07
Patent number
US05539114

Reaction notes

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