Benzenesulfonyl chloride, 4-chloro-3-nitro- → HCID 5016179, compound

HRID 883975Notes

Reaction equation

HRID 883975 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=2)(=[O:10])=[O:9])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 78074-BromoanilineHCID 517045Sodium Acetate

Product 1

HCID 5016179HCID 5016179, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-chloro-3-nitrobenzenesulfonyl chloride (2.561 g, 10 mmol) in acetic acid (20 mL) was treated with 4-bromoaniline (1.72 g, 10 mmol) and anhydrous sodium acetate (1.23 g, 15 mmol), then heated at 100° for 30 minutes. The reaction was cooled to room temperature and the acetic acid removed by rotary evaporation under vacuum. The residue was taken up in ethyl acetate (100 mL) and washed with water (2×25 mL) and brine (25 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum, co-evaporating the oil with methylene chloride/hexanes. Purification by silica gel chromatography using methylene chloride followed by 5% ethyl acetate/methylene chloride as eluent provided the title compound as a yellow solid (2.038 g, 52%).

Workup

  1. temperatureheated at 100° for 30 minutes
  2. customthe acetic acid removed by rotary evaporation under vacuum
  3. washwashed with water (2×25 mL) and brine (25 mL)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-29186f3e11e840f1aa5f0dae5433c6f2
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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