Hydrochloric Acid → HCID 117652594, compound

HRID 1428386Notes

Reaction equation

HRID 1428386 reaction equation
[Cl:1][C:2]1[C:3]([F:14])=[C:4]([NH:9][C:10](=[O:13])[O:11]C)[C:5](O)=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[O:11][C:10](=[O:13])[NH:9][C:4]=2[C:3]=1[F:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 117662396HCID 117662396, compound

Product 1

HCID 117652594HCID 117652594, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of methyl (3-chloro-2-fluoro-6-hydroxyphenyl)carbamate (173 mg) and DMF (1.5 mL) was added K2CO3 (218 mg), followed by heating and stirring at 120° C. for 20 minutes. The reaction mixture was cooled to room temperature, and then added to ice water. To the reaction mixture was added concentrated hydrochloric acid (263 μL) under ice-cooling, followed by stirring at the same temperature for 30 minutes. The resulting solid was collected by filtration and then washed with water to obtain 5-chloro-4-fluoro-1,3-benzoxazol-2(3H)-one (117 mg).

Workup

  1. temperatureby heating
  2. temperatureThe reaction mixture was cooled to room temperature
  3. temperaturecooling
  4. stirringby stirring at the same temperature for 30 minutes
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-9aec2e793bbe49f6a44e1394d27f3eca
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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