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

HRID 1735966노트

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HRID 1735966 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+]>C1(C)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: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 90.3%

시약·촉매·용매 1

HCID 7237O-Xylene용매2회

반응 조건

온도
90 °C

실험 절차

A solution of 2,4-dichlorophenyl isocyanate (47.0 g, 0.25 mol) in xylene (130 ml) is metered at room temperature into a solution of ethyl 5-fluoroanthranilate (45.2 g, 0.25 mol) in xylene (210 ml). After addition is complete, the mixture is stirred at 90° C. for 2.5 hours. 4.50 ml of a 30% strength solution of methanolic sodium methoxide (0.025 mol) are metered in and the mixture is stirred at 90° C. for a further 2 hours, ethanol and methanol being distilled off. After cooling, the product is filtered off with suction and washed with 3×30 ml of xylene. The xylene-moist precipitate is treated with dilute hydrochloric acid and the residual xylene is removed by azeotropic distillation. The product is then filtered off with suction, washed with water and dried. 73.4 g of 3-(2,4 dichlorophenyl)-6-fluoro-2,4(1H,3H)-quinazolinedione (yield: 90.3% of theory) of melting point 313° to 314° C. are obtained.

후처리

  1. additionAfter addition
  2. stirringis stirred at 90° C. for a further 2 hours
  3. distillationethanol and methanol being distilled off
  4. temperatureAfter cooling
  5. filtrationthe product is filtered off with suction
  6. washwashed with 3×30 ml of xylene
  7. additionThe xylene-moist precipitate is treated with dilute hydrochloric acid
  8. customthe residual xylene 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-868557d3a0e54c1d94fa5c5bd6352598
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05539114

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