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2-Methoxyethanol → 3-[3-(4-Hydroxy-5-oxo-2-phenyl-2-imidazolin-4-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 49000
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HRID 49000 반응식
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21](=[O:25])[C:22]([O-])=[O:23])[C:17]=3[CH:26]=2)[C:3]1=[O:27].CO[CH2:30][CH2:31]O>O>[OH:25][C:21]1([C:18]2[C:17]3[CH:26]=[C:13]([N:4]4[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:11])([F:9])[F:10])[N:2]([CH3:1])[C:3]4=[O:27])[CH:14]=[CH:15][C:16]=3[S:20][N:19]=2)[C:22](=[O:23])[NH:4][C:3]([C:31]2[CH:30]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 80192-MethoxyethanolHCID 206342715-[3-,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-glyoxylate

생성물 1

HCID 206342263-[3-(4-Hydroxy-5-oxo-2-phenyl-2-imidazolin-4-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil수율 14.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 5-[3-,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-glyoxylate (0.620 g, 1.50 mmol), phenyl amidine hydrochloride (0.258 g, 1.65 mmol) and 2-methoxyethanol is stirred 40 minutes at reflux, cooled to room temperature and poured into water. The resultant yellow precipitate is filtered and saved. The filtrate is extracted four times with methylene chloride; the combined organic layers are concentrated in vacuo and the residue is triturated with ether to afford a yellow solid. The yellow solids are combined and chromatographed on silica gel with methylene chloride-methanol to afford the title compound as a solid (0.110 g, 14.6%, mp 139-141° C.) which is identified by NMR spectral analysis.

후처리

  1. temperatureat reflux
  2. filtrationThe resultant yellow precipitate is filtered
  3. extractionThe filtrate is extracted four times with methylene chloride
  4. concentrationthe combined organic layers are concentrated in vacuo
  5. customthe residue is triturated with ether
  6. customto afford a yellow solid
  7. customchromatographed on silica gel with methylene chloride-methanol

출처 및 근거

ORD 기록
ord-6f088f4d7dfb4b76bbec0ba05b82ec18
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06706663B2

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