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Nitric Acid → 3-(4-Chloro-2-methyl-3-nitrobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

HRID 366338
Notes
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Reaction equation

HRID 366338 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:4][CH:3]=1.[N+:25]([O-])([OH:27])=[O:26]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]2[C:8]([N+:25]([O-:27])=[O:26])=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 232891903-(4-Chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

Product 1

HCID 232891773-(4-Chloro-2-methyl-3-nitrobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracilYield 67.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-20 °C

Procedure

0.5 g (1.4 mmol) of 3-(4-chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 10 ml of concentrated sulfuric acid, and 0.1 g (1.1 mmol) of 60% nitric acid was dropwise added thereto at -20° C. After stirring at -20° C. for 10 minutes, the reaction solution was poured into ice water and extracted with 50 ml of chloroform. 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 0.3 g (yield: 53.3%) of the desired product as a pale yellow crystals. Melting point: 174-175° C.

Workup

  1. customat -20° C
  2. extractionextracted with 50 ml of chloroform
  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-b281e38e2eef4d488ca398f0ead348ac
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