Pyridine → HCID 4202153, compound

HRID 230538Notes

Reaction equation

HRID 230538 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].[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]([Cl:15])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 79323-Chloroaniline

Product 1

HCID 4202153HCID 4202153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chloro-3-nitrobenzenesulfonylchloride (1 g, 3.9 mmol), 3-chloroaniline (0.5 mL, 4.7 mmol) and pyridine (1.6 mL) in CH2Cl2 (2 mL) was stirred at room temperature. The reaction was quenched with NaHCO3 (sat aq solution, 30 mL×3). The organic phase was separated, dried (MgSO4), and filtered. The volatiles were evaporated and the residue was purified by column chromatography (SiO2, pentane:EtOAc, 4:1) to give 4-chloro-N-(3-chlorophenyl)-3-nitrobenzenesulfonamide; MS (posESI) m/z=349.2 (M+H+).

Workup

  1. customThe reaction was quenched with NaHCO3 (sat aq solution, 30 mL×3)
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe volatiles were evaporated
  6. customthe residue was purified by column chromatography (SiO2, pentane:EtOAc, 4:1)

Sources & evidence

ORD record
ord-f8e3783d49ea418da24a6b54c6ba3c71
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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