Pyridine → HCID 69548666, compound

HRID 433339Notes

Reaction equation

HRID 433339 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:11](Cl)(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10])([O-])=O.[Cl:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:10][C:9]1[CH:8]=[CH:7][C:6]([S:11]([C:16]2([Cl:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:17]2[NH2:18])(=[O:13])=[O:12])=[CH:5][C:4]=1[NH2:1]

Participants

6

Reactant 3

HCID 1049PyridineHCID 72402-ChloroanilineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-

Product 1

HCID 69548666HCID 69548666, compoundYield 14.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-nitro-4-chlorobenzenesulphonyl chloride (768 mg, 3.0 mmol), 2-chloroaniline (383 mg, 3.0 mmol), 4-dimethylaminopyridine (10 mg, 0.08 mmol) and pyridine (0.30 ml, 3.6 mmol) in DCM (35 ml) was stirred at ambient temperature overnight. The solution was evaporated to dryness, the residue dissolved in EtOAc and washed with 1.0 M aqueous hydrochloric acid and brine, dried and evaporated to dryness. The residue was dissolved in EtOAc (30 ml) and hydrogenated over 10% Pd/C for 4 h at ambient temperature. The catalyst was removed by filtration and the EtOAc evaporated to dryness. The residue was purified by column chromatography on basic alumina using 5% methanol in EtOAc to give, as a solid, the title compound (140 mg, 0.44 mmol). MS: 315.

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with 1.0 M aqueous hydrochloric acid and brine
  4. customdried
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in EtOAc (30 ml) and hydrogenated over 10% Pd/C for 4 h at ambient temperature
  7. customThe catalyst was removed by filtration
  8. customthe EtOAc evaporated to dryness
  9. customThe residue was purified by column chromatography on basic alumina using 5% methanol in EtOAc
  10. customto give, as a solid

Sources & evidence

ORD record
ord-66292960cf934caeb689993caba5d0a7
Source dataset
uspto-grants-2003_12
Patent number
US06667342B1

Reaction notes

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