Sulfuric Acid → HCID 15477226, compound

HRID 366317Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11](Br)Br)[O:10][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1.S(=O)(=O)(O)[OH:29]>>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]=[O:29])[O:10][C:6]=2[C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 23289158HCID 23289158, compound

Product 1

HCID 15477226HCID 15477226, compoundYield 88.4%

Conditions

Temperature: 50 °C

Procedure

60 ml of concentrated sulfuric acid was added to 12.0 g (22.5 mmol) of 3-(4-chloro-2-dibromomethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, followed by stirring at 50° C. for 1 hour. After completion of the reaction, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution, water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was crystallized from isopropyl ether to obtain 7.6 g (yield: 88.4%) of the desired product as pale yellow crystals. Melting point: 180-183° C.

Workup

customAfter completion of the reaction
extractionextracted with ethyl acetate
washThe organic layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution, water
dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customThen, the obtained residue was crystallized from isopropyl ether

Sources & evidence

ORD record: ord-b55b7b877b0e4a8a84cdad071b101e0c
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130187

Reaction notes

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