p-Toluenesulfonic acid → HCID 117652630, compound

HRID 634056Notes

Reaction equation

HRID 634056 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH3:9])[CH:5]=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:13]=1[NH2:14].CC1C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Cl-].[Ca+2]>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[N:14][C:13]2[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:12]=2[CH3:11])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 69132,4,6-TrimethylanilineHCID 5284359Calcium ChlorideHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 117652630HCID 117652630, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In argon atmosphere, a mixture of 3.70 g (18.50 mmol) of 1-(6-bromopyridin-2-yl)ethanone, 2.49 g (18.50 mmol) of 2,4,6-trimethylaniline, 50 mg of TsOH, and 150 ml of toluene was refluxed for 2.5 h using a Soxhlet apparatus with an extraction thimble filled with anhydrous CaCl2. The resulting mixture was cooled to ambient temperature, passed through a short layer of silica gel 60 (40-63 um), and then evaporated to dryness. Yield 5.59 g (95%) of dark-red solid. Anal. calc. for C16H17BrN2: C, 60.58; H, 5.40; N, 8.83. Found: C, 60.70; H, 5.56; N, 8.77. 1H NMR (CDCl3): δ 7.98 (dd, J=7.1 Hz, J=1.4 Hz, 1H, 3-H in pyridine), 7.63-7.71 (m, 2H, 4, 5-H in pyridine), 6.76 (s, 2H, 3, 5-H in mesityl), 2.70 (s, 3H, MeC═N), 2.20 (s, 3H, 4-Me in mesityl), 2.15 (s, 6H, 2, 6-Me in mesityl).

Workup

  1. temperaturewas refluxed for 2.5 h
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-c5ec61f96a284baf9cd6daa8b8ddf5ee
Source dataset
uspto-grants-2016_04
Patent number
US09321858B2

Reaction notes

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