p-Toluenesulfonic acid → HCID 15292071, compound

HRID 2396750Notes

Reaction equation

HRID 2396750 reaction equation
[C:1]1([CH2:7][C:8](Cl)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1[C:13]([NH:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:14]([NH2:34])[C:15]([N:19]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:16][C:17]=1[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:18][C:17]1[N:16]=[C:15]([N:19]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:14]2[N:34]=[C:36]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:35]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:13]=2[C:12]=1[CH3:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7679Phenylacetyl chlorideHCID 54380635HCID 54380635, compound

Product 1

HCID 15292071HCID 15292071, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylacetyl chloride (0.6 mL, 4.5 mmole) was added to a solution of 5,6-dimethyl-N4 -(2-phenylethyl)-N2,N2 -bis(phenylmethyl)pyridine-2,3,4-triamine (1.96 g, 4.5 mmole) in methylene chloride (100 mL) and the resulting mixture was stirred at ambient temperature overnight. A catalytic amount of p-toluenesulfonic acid was added and stirring was continued at ambient temperature over the weekend. The reaction mixture was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate then concentrated under vacuum to provide an oil. The oil was purified by silica gel column chromatography eluting with 5-10% ethyl acetate in hexane to provide 1.8 g of the desired product as a white solid, m.p. 139°-141° C. Analysis: Calculated for C37H36N4 : % C, 82.80; % H, 6.76; % N, 10.44; Found: % C, 82.86; % H, 6.78; % N, 10.36.

Workup

  1. stirringstirring
  2. customwas continued at ambient temperature over the weekend
  3. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationthen concentrated under vacuum
  6. customto provide an oil
  7. customThe oil was purified by silica gel column chromatography
  8. washeluting with 5-10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d7cbcf4b469848e19187215e3438d9c5
Source dataset
uspto-grants-1996_02
Patent number
US05494916

Reaction notes

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