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Malonic Acid → 1-Cyclopropyl-3-(2-fluoro-4-iodophenyl)pyrimidine-2,4,6-trione

HRID 75649
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HRID 75649 반응식
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=2[F:15])=[O:6])[CH2:3][CH2:2]1.[C:16](O)(=[O:21])[CH2:17][C:18](O)=[O:19].C(OC(=O)C)(=O)C.C(Cl)(=O)C>O.C1(C)C=CC=CC=1>[CH:1]1([N:4]2[C:18](=[O:19])[CH2:17][C:16](=[O:21])[N:7]([C:8]3[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=3[F:15])[C:5]2=[O:6])[CH2:2][CH2:3]1
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참가 물질

6

반응물 4

HCID 867Malonic AcidHCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 59717054N-Cyclopropyl-N'-(2-fluoro-4-iodophenyl)urea

생성물 1

HCID 597172111-Cyclopropyl-3-(2-fluoro-4-iodophenyl)pyrimidine-2,4,6-trione수율 82.3%

시약·촉매·용매 1

HCID 22272177
Toluene water
용매

반응 조건

온도
60 °C

실험 절차

To 1-cyclopropyl-3-(2-fluoro-4-iodophenyl)urea 48 (61.0 g) obtained in Step 1 and malonic acid 4 (19.9 g) were added acetic anhydride (300 ml) and acetyl chloride (27.2 ml), and the mixture was stirred under a nitrogen atmosphere at 60° C. for 3 hrs. After allowing to cool to room temperature, the reaction mixture was added dropwise to water-toluene [2:1 (volume ratio), 900 ml] with stirring. The precipitated crystals were collected by filtration and dried to give 1-cyclopropyl-3-(2-fluoro-4-iodophenyl)pyrimidine-2,4,6-trione 49 (60.9 g, yield 82%) as pale-yellow crystals.

후처리

  1. temperatureto cool to room temperature
  2. stirringwith stirring
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried

출처 및 근거

ORD 기록
ord-98b987ece858456f86306871045cc49e
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835443B2

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