Hydrochloric Acid → HCID 18422222, compound

HRID 1281865Notes

Reaction equation

HRID 1281865 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:16]=[CH:15][S:14][C:13]=2Br)=[O:11])[C:5]([OH:8])=[CH:6][CH:7]=1.[C:18](=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][C:13]3[S:14][C:15]([CH3:18])=[CH:16][C:12]=3[C:10](=[O:11])[NH:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 18422332HCID 18422332, compound

Product 1

HCID 18422222HCID 18422222, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of N-(3-fluoro-6-hydroxyphenyl)-2-bromo-3-thiophenecarboxamide (3.3 g) in dimethyl sulfoxide (100 ml) was added potassium carbonate (2.8 g) and the mixture was stirred at 140° C. for 1 hour. The reaction system was cooled to room temperature and the reaction mixture was poured into diluted hydrochloric acid under ice-cooling. The precipitated crystals were collected by filtration, dissolved in chloroform, washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=99.5:0.5). The solvent was evaporated under reduced pressure. To the residue was added ethyl acetate and the precipitated crystals were collected by filtration to give 7-fluoro-2-methylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (350 mg).

Workup

  1. temperatureThe reaction system was cooled to room temperature
  2. temperaturecooling
  3. filtrationThe precipitated crystals were collected by filtration
  4. dissolutiondissolved in chloroform
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=99.5:0.5)
  9. customThe solvent was evaporated under reduced pressure
  10. additionTo the residue was added ethyl acetate
  11. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-f0c4e60b28ba457eba92eaf5c9c60d42
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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