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

HRID 1735967노트

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HRID 1735967 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 40212773-(2,4-Dichlorophenyl)-6-fluoroquinazoline-2,4(1H,3H)-dione수율 97.5%

시약·촉매·용매 1

HCID 180Acetone용매2회

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-75d516541d77403a8c767c83673423dd
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05539114

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