4-Fluoroaniline → 152721-97-6

HRID 2112560Notes

Reaction equation

HRID 2112560 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](CC)([O-])=O.[N+](C)([O-])=O>[F:8][C:9]1[CH:15]=[CH:14][C:12]2[NH:13][C:6](=[O:7])[NH:5][S:2](=[O:4])(=[O:3])[C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 97314-FluoroanilineHCID 70918Chlorosulfonyl isocyanateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11096006152721-97-6

Reagents, catalysts & solvents 2

HCID 6375NitromethaneSolventHCID 6587NitroethaneSolvent

Conditions

Temperature
-80 °C

Procedure

After dissolving chlorosulfonyl isocyanate (3.29 mL, 37.8 mmol) in nitroethane (45 mL), the mixture was cooled to −80° C. A solution of 4-fluoroaniline (3.50 g, 31.5 mmol) in nitromethane (5 mL) was then added dropwise thereto over a period of 10 minutes. The reaction mixture was raised to 0° C., and aluminum chloride (5.33 g, 40.0 mmol) was added. After heating to reflux for 30 minutes, the reaction mixture was cooled to room temperature and poured into ice water (120 mL). The precipitated crystals were filtered out and dried to obtain 7-fluoro-2H,4H-benzo[e]1,2,4-thiadiazine-1,1,3-trione.

Workup

  1. temperatureThe reaction mixture was raised to 0° C.
  2. temperatureAfter heating
  3. temperatureto reflux for 30 minutes
  4. temperaturethe reaction mixture was cooled to room temperature
  5. filtrationThe precipitated crystals were filtered out
  6. customdried

Sources & evidence

ORD record
ord-74abfad711174d87a9dd273e528c5148
Source dataset
uspto-grants-2009_04
Patent number
US07524841B2

Reaction notes

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