Pyridine → HCID 86589563, compound

HRID 916743Notes

Reaction equation

HRID 916743 reaction equation
[N+](C1C=C(C2[NH:14][C:13]3[CH:15]=[CH:16][C:17]([C:19](N)=[O:20])=[CH:18][C:12]=3N=2)C=CC=1)([O-])=O.NC1C=CC(C=O)=CC=1.N1C=CC=CC=1.[Cl:37][C:38]1[CH:39]=[C:40]([S:45](Cl)(=[O:47])=[O:46])[CH:41]=[CH:42][C:43]=1[Cl:44]>C(Cl)Cl>[Cl:37][C:38]1[CH:39]=[C:40]([S:45]([NH:14][C:13]2[CH:12]=[CH:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=2)(=[O:46])=[O:47])[CH:41]=[CH:42][C:43]=1[Cl:44]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 111584-AminobenzaldehydeHCID 178513578HCID 178513578, compound

Product 1

HCID 86589563HCID 86589563, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Nitro-phenyl)-1H-benzoimidazole-5-carboxylic acid amide. To a flask containing crude 4-amino-benzaldehyde (100 mg, 0.82 mmol), pyridine (0.15 mL, 1.87 mmol) and CH2Cl2 (4 mL), was added 3,4-dichlorobenzenesulfonyl chloride (184 mg, 0.75 mmol). The mixture was stirred for 16 h at room temperature, and was then cooled and concentrated. The crude product was purified by silica gel flash chromatography (eluted with 5% methanol/CH2Cl2) to provide 179 mg (72%) of 3,4-dichloro-N-(4-formyl-phenyl)-benzenesulfonamide.

Workup

  1. temperaturewas then cooled
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel flash chromatography (eluted with 5% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-5e3e9ef6c75544458dfa3b4eab7d98db
Source dataset
uspto-grants-2007_09
Patent number
US07271261B2

Reaction notes

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