Water → HCID 22316620, compound

HRID 497258Notes

Reaction equation

HRID 497258 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[C:15]([F:23])[CH:14]=3)[N:11]=[CH:10][C:9]=2[N+:24]([O-])=O)=[CH:4][CH:3]=1.[NH4+].[Cl-].O>CCO.[Fe]>[NH2:24][C:9]1[CH:10]=[N:11][N:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[C:15]([F:23])[CH:14]=2)[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 22316681HCID 22316681, compound

Product 1

HCID 22316620HCID 22316620, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-(4-bromophenyl)-1-[3-fluoro-4-(methylsulfonyl)phenyl]-4-nitro-1H-pyrazole from step 2 (2.5 g, 5.7 mmol), iron powder (1.6 g, 28.4 mmol) and NH4Cl (30 mg, 0.57 mmol) in EtOH:H2O (40 mL: 10 mL) was refluxed for 1 h. After cooled to room temperature, the mixture was filtered by celite and washed with ethyl acetate and the filtrate was concentrated. Water (50 mL) was added to the residual oil and extracted with ethyl acetate (80 mL), dried over MgSO4, and concentrated in vacuo gave the title-compound (1.9 g, 82%).

Workup

  1. filtrationthe mixture was filtered by celite
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. additionWater (50 mL) was added to the residual oil
  5. extractionextracted with ethyl acetate (80 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f341622e6314684b5eece2cab878a4d
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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