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

HRID 1735969노트

반응식

HRID 1735969 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+]>CN1CCCC1=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 91.7%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매2회

반응 조건

온도
90 °C

실험 절차

A solution of 2,4-dichlorophenyl isocyanate (18.8 g, 0.10 mol) in N-methylpyrrolidone (50 ml) is metered at room temperature into a solution of ethyl 5-fluoroanthranilate (18.3 g, 0.10 mol) in N-methylpyrrolidone (70 ml). After addition is complete, the mixture is stirred at 90° C. for 2 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, ethanol and methanol being distilled off. After cooling, the product is precipitated by addition of dilute hydrochloric acid (100 ml). The product is then filtered off with suction, washed with water and dried. 29.8 g of 3-(2,4-dichlorophenyl)-6-fluoro-2,4(1H,3H)-quinazolinedione (yield: 91.7% of theory) of melting point 311° to 313° C. are obtained.

후처리

  1. additionAfter addition
  2. stirringis stirred
  3. temperatureunder reflux for a further 2 hours
  4. distillationethanol and methanol being distilled off
  5. temperatureAfter cooling
  6. customthe product is precipitated by addition of dilute hydrochloric acid (100 ml)
  7. filtrationThe product is then filtered off with suction
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-5ccbc9feb3244fffa980c2b49e62b9cc
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05539114

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