Benzenesulfonyl chloride → HCID 2838317, compound

HRID 1006544Notes

Reaction equation

HRID 1006544 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+].[Cl-].[NH4+]>>[C:15]1([S:21]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67865Benzenamine, 2-nitro-4-(trifluoromethyl)-

Product 1

HCID 2838317HCID 2838317, compoundYield 93.6%

Procedure

To a solution of 4-amino-3-nitrobenzotrifluoride (3.09 g) in THF sodium hydride (660 mg) was added. The mixture was stirred for 30 minutes at room temperature. After stirring, benzenesulfonylchloride (3.18 g) was added thereto. The mixture was stirred for 2 hours at room temperature. In addition, sodium hydride (420 mg) was added thereto. The mixture was stirred for 1 hour. The reaction mixture was acidified by adding an aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was washed, dried over, filtered and concentrated to give the title compound (4.86 g) having the following physical data.

Workup

  1. stirringAfter stirring
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. stirringThe mixture was stirred for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed
  6. customdried over,
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-846c0378a2d44c4cabcb7c4b60f9a2c7
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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