4-Nitrobenzenesulfonyl chloride → HCID 58896227, compound

HRID 1393908Notes

Reaction equation

HRID 1393908 reaction equation
[O:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=2)=[CH:4][N:3]=[CH:2]1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14]>N1C=CC=CC=1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([C:5]3[O:1][CH:2]=[N:3][CH:4]=3)[CH:7]=2)(=[O:24])=[O:23])=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 27392893-(1,3-Oxazol-5-yl)aniline

Product 1

HCID 58896227HCID 58896227, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-oxazol-5-yl-phenylamine (0.5 g, 3.1 mmol) and 4-nitro-benzenesulfonyl chloride (0.91 g, 4.1 mmol) in pyridine (20 ml) was stirred over weekend at room temperature. The residue was partitioned between EtOAc and H2O. The organic layer was separated, washed twice with H2O and once with saturated aqueous sodium chloride solution, dried and concentrated by evaporation. The residue was purified by column chromatography on silica-gel (5%-15% EtOAc-hexane) to afford 0.63 g of product.

Workup

  1. customThe residue was partitioned between EtOAc and H2O
  2. customThe organic layer was separated
  3. washwashed twice with H2O and once with saturated aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated by evaporation
  6. customThe residue was purified by column chromatography on silica-gel (5%-15% EtOAc-hexane)

Sources & evidence

ORD record
ord-39ce3338613e43cca8314c34a712c9a4
Source dataset
uspto-grants-2008_03
Patent number
US07348322B2

Reaction notes

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