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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
Notes
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Reaction equation

HRID 49000 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6f088f4d7dfb4b76bbec0ba05b82ec18
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06706663B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes