Water → HCID 22316620, compound

HRID 1597566Notes

Reaction equation

HRID 1597566 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 step2 (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 concentarted 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),dried over MgSO4

Sources & evidence

ORD record
ord-fcf0e2946b2f48afb07718491489d5ee
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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