Formic Acid → 3-(4-bromo-2-fluorobenzyl)-7-chloro-2,4(1H,3H)-quinazolinedione

HRID 726843

반응식

HRID 726843 반응식
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N:7]=[C:8]=[O:9])=[C:4]([F:12])[CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([NH2:24])[C:17](=[CH:22][CH:23]=1)[C:18](OC)=[O:19].C[O-].[Na+].C(O)=O>C1(C)C(C)=CC=CC=1.CO>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N:7]2[C:18](=[O:19])[C:17]3[C:16](=[CH:15][C:14]([Cl:13])=[CH:23][CH:22]=3)[NH:24][C:8]2=[O:9])=[C:4]([F:12])[CH:3]=1

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 80001Methyl 4-chloroanthranilateHCID 10942334Sodium MethoxideHCID 158174014-Bromo-2-fluoro-1-(isocyanatomethyl)benzene

생성물 1

HCID 144237993-(4-bromo-2-fluorobenzyl)-7-chloro-2,4(1H,3H)-quinazolinedione수율 86.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 7237O-Xylene용매2회

반응 조건

온도
110 °C

실험 절차

A solution of 4-bromo-2-fluorobenzyl isocyanate (46.0 g, 0.20 mol) in xylene (100 ml) is metered, at room temperature, into a solution of methyl 4-chloroanthranilate (37.1 g, 0.20 mol) in xylene (250 ml). After the addition has ended, the batch is stirred at 110° C. for 2 hours. 3.60 ml of a 30% solution of methanolic sodium methylate (0.020 mol) are metered in and the mixture is stirred at 90° C. for 2 hours, during which process methanol is distilled off. 1.8 ml of 85% formic acid (0.040 mol) are subsequently added, and the mixture is stirred at 90° C. for a further hour. After cooling, the product is filtered off with suction, washed with 3×50 ml of xylene, 3×50 ml of ethanol and 3×100 ml of water, and dried. 66.1 g of 3-(4-bromo-2-fluorobenzyl)-7-chloro-2,4(1H,3H)-quinazolinedione (yield: 86.2% of theory) of melting point 288 ° to 289° C. (lit. >280° C.) are obtained.

후처리

  1. additionAfter the addition
  2. stirringis stirred at 90° C. for 2 hours, during which
  3. distillationis distilled off
  4. stirringthe mixture is stirred at 90° C. for a further hour
  5. temperatureAfter cooling
  6. filtrationthe product is filtered off with suction
  7. washwashed with 3×50 ml of xylene, 3×50 ml of ethanol and 3×100 ml of water
  8. customdried

출처 및 근거

ORD 기록
ord-f45fee0d704a4d0f8a99a6d29102c84a
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05710319

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