3-Chloroaniline → HCID 59982349, compound

HRID 606270Notes

Reaction equation

HRID 606270 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Cl:9][C:10]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:11]=1[O:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([S:20](Cl)(=[O:22])=[O:21])=[CH:15][C:14]=1[Cl:24]>N1C=CC=CC=1>[Cl:24][C:14]1[CH:15]=[C:16]([S:20]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=2)(=[O:22])=[O:21])[CH:17]=[C:18]([Cl:19])[C:13]=1[O:12][C:11]1[CH:25]=[CH:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:10]=1[Cl:9]

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 27743613,5-Dichloro-4-(2-chloro-4-nitrophenoxy)benzene-1-sulfonyl chloride

Product 1

HCID 59982349HCID 59982349, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-chloroaniline (38 μL, 0.35 mmol) and 4-(2-chloro-4-nitrophenoxy)-3,5-dichloro-benzenesulfonyl chloride (100 mg, 0.24 mmol), was stirred in pyridine (2 mL) at room temperature for three days. The reaction mixture was concentrated by rotary evaporator and dissolved in dichloromethane. The solution was washed successively with 1N HCl, and NaHCO3 (sat.)/brine. The organic fraction was dried over MgSO4, filtered, and concentrated. The compound was purified by radial silica gel chromatography (1:20 to 1:1 ethyl acetate:hexanes) to afford the product which was subsequently freeze-dried from H2O/acetonitrile to produce a white solid which was 97% pure by LCMS analysis (67 mg, 55%).

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporator
  2. dissolutiondissolved in dichloromethane
  3. washThe solution was washed successively with 1N HCl, and NaHCO3 (sat.)/brine
  4. dry with materialThe organic fraction was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe compound was purified by radial silica gel chromatography (1:20 to 1:1 ethyl acetate:hexanes)
  8. customto afford the product which
  9. dry with materialwas subsequently freeze-dried from H2O/acetonitrile
  10. customto produce a white solid which

Sources & evidence

ORD record
ord-1966440301a645439eeac686eb9a73db
Source dataset
uspto-grants-2011_03
Patent number
US07915293B2

Reaction notes

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