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Dimethylformamide → 3-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-1-amino-6-trifluoromethyluracil

HRID 366316
Notes
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Reaction equation

HRID 366316 reaction equation
C[N:2](C)C=O.[Cl:6][C:7]1[C:12]2[CH:13]=[C:14]([CH2:16][CH3:17])[O:15][C:11]=2[C:10]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[NH:20][C:19]2=[O:29])=[C:9]([F:30])[CH:8]=1.[N+](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:6][C:7]1[C:12]2[CH:13]=[C:14]([CH2:16][CH3:17])[O:15][C:11]=2[C:10]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[N:20]([NH2:2])[C:19]2=[O:29])=[C:9]([F:30])[CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 232891763-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil

Product 1

HCID 232891653-(4-Chloro-2-ethyl-6-fluorobenzofuran-7-yl)-1-amino-6-trifluoromethyluracilYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

80 ml of N,N-dimethylformamide was added to 3.4 g (9.0 mmol) of 3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil, 2.7 g (14 mmol) of 2,4-dinitrophenoxyamine and 5.0 g (36 mmol) of potassium carbonate, followed by stirring at 60 to 70° C. for 1 hour. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 2.0 g (yield: 58%) of the desired product as white crystals. Melting point: 145-147° C.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water
  4. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6b136cb4a742421583c4eabc5cf768e4
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06130187

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes