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Hydrochloric Acid → 2-{2-(Methoxycarbonyl)methoxyphenoxy}-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene

HRID 1280350
Notes
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Reaction equation

HRID 1280350 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])=[O:4].F[C:15]1[CH:20]=[C:19]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[N:23]([CH3:32])[C:22]2=[O:33])[C:18]([F:34])=[CH:17][C:16]=1[N+:35]([O-:37])=[O:36].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:15]1[CH:20]=[C:19]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[N:23]([CH3:32])[C:22]2=[O:33])[C:18]([F:34])=[CH:17][C:16]=1[N+:35]([O-:37])=[O:36])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23202292-(Methoxycarbonyl)methoxyphenol2×HCID 121155092,5-Difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene

Product 1

HCID 187592902-{2-(Methoxycarbonyl)methoxyphenoxy}-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene
Yield 41.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15.16 g of 2-(methoxycarbonyl)methoxyphenol, 29.23 g of 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene (produced in Intermediate Production Example 4), 11.5 g of anhydrous potassium carbonate and 160 ml of N,N-dimethylformamide was stirred at room temperature for 30 minutes, and then, stirred at 70° C. for 3 hours. To the mixture, 5 g of 2-(methoxycarbonyl)methoxyphenol was added and stirred for 1 hour. The reaction solution was poured into 2% of aqueous hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 17.8 g of 2-{2-(methoxycarbonyl)methoxyphenoxy}-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene [Compound 4-19 of the present invention].

Workup

  1. stirringstirred at 70° C. for 3 hours
  2. stirringstirred for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-833a6d657f9947d195c728c9efa05c5e
Source dataset
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06451740B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes