3-Pyridinecarboxaldehyde → HCID 54199306, compound

HRID 853784Notes

Reaction equation

HRID 853784 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([N:19]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:17])=[O:18])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 668244-Chlorobenzenesulfonamide

Product 1

HCID 54199306HCID 54199306, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-pyridine-carboxaldehyde (2.6 g, 24.2 mmol) and 4-chlorobenzenesulfonamide (5.0 g, 26.0 mmol) in toluene was added powdered molecular sieve 4A (2.5 g) and AMBERLYST H+ (2.5 g). The reaction mixture was heated in a Dean-Stark apparatus for 16 h. After cooling to room temperature, the mixture was filtered through a pad of CELITE. The CELITE was washed with EtOAc, and the filtrate was concentrated to give 6.4 g (94%) of the title product as a white solid. 1H NMR (CDCl3 300 MHz) δ 9.12 (1H, s), 9.06 (1H, s), 8.83 (1H, m), 8.28 (1H, m), 7.95 (2H, d), 7.55 (2H, d), 7.47 (1H, m), MS (ES) m/e 280.5 (M)+.

Workup

  1. temperatureThe reaction mixture was heated in a Dean-Stark apparatus for 16 h
  2. filtrationthe mixture was filtered through a pad of CELITE
  3. washThe CELITE was washed with EtOAc
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cdf13759f44140098e333961277ad388
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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