p-Toluenesulfonic acid → HCID 46841411, compound

HRID 1846335Notes

Reaction equation

HRID 1846335 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=[O:5].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][N:20]=1.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CC(N(C)C)=O.C(OCC)(=O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:1]=[C:23]2[C:22]2[CH:21]=[N:20][C:19]([Cl:18])=[CH:26][CH:25]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6704722-amino-N-(4-chlorophenyl)benzamideHCID 27640536-Chloropyridine-3-carbaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 46841411HCID 46841411, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Amino-N-(4-chlorophenyl)benzamide (0.500 g, 2.03 mmol) and 6-chloronicotinaldehyde (2.23 mmol), NaHSO3 (0.253 g, 2.44 mmol) and p-TsOH (0.039 g, 0.20 mmol) were dissolved in DMA (20 mL) and heated at 150° C. for 21 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with water (2×200 mL), dried (Na2SO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 70% ethyl acetate/heptane, afforded the title compound as a white solid (4%). 1H-NMR (300 MHz, DMSO-6): δ 8.46 (d, J=2.1 Hz, 1H), 8.23 (d, J=8.1 Hz, 1H), 7.92-7.97 (m, 1H), 7.80-7.86 (m, 2H), 7.63-7.68 (m, 1H), 7.47-7.50 (m, 5H). MS (APCI) m/z: 368 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water (2×200 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washFlash chromatograph on silica gel, eluting with 30% ethyl acetate/heptane to 70% ethyl acetate/heptane

Sources & evidence

ORD record
ord-0332d946e87041bcabe31fb53b986635
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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