p-Toluenesulfonic acid → HCID 178499497, compound

HRID 574346Notes

Reaction equation

HRID 574346 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]=[N:10][CH:9]([NH2:12])[N:8]=2)[CH:2]=1.[C:19]([CH:22]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:23](OC)=[O:24])(=O)[CH3:20].S(O)(C1C=CC(C)=CC=1)(=O)=O>C1(C)C(C)=CC=CC=1>[C:1]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[C:9]3[N:12]=[C:19]([CH3:20])[C:22]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:23]([OH:24])[N:10]3[N:11]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 112039Dimethyl acetylsuccinateHCID 866950725-([1,1'-biphenyl]-3-yl)-3H-1,2,4-triazol-3-amine

Product 1

HCID 178499497HCID 178499497, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In a 100 ml RBF, equipped with a Dean-Stark trap (filled with molecular sieves), was added 5-([1,1′-biphenyl]-3-yl)-3H-1,2,4-triazol-3-amine (1.133 g, 4.80 mmol), dimethyl 2-acetylsuccinate (2.334 mL, 14.39 mmol) followed by Xylene (50 mL) and Ts-OH (9.12 mg, 0.048 mmol). The reaction was heated at reflux for 5 hrs. Filtered and washed by hexanes to collect the off-white solid, which was used directly for the next step. 1H-NMR (500 MHz, CDCl3) δ 2.26 (3H, s), 3.65 (2H, s), 3.72 (3H, s), 7.35-7.36 (1H, m), 7.44-7.46 (2H, m), 7.47-7.48 (1H, m), 7.64-7.66 (2H, m), 7.73-7.75 (1H, m), 8.13-8.15 (1H, m), 8.43 (1 H, s).

Workup

  1. customIn a 100 ml RBF, equipped with a Dean-Stark trap (filled with molecular sieves)
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 5 hrs
  4. filtrationFiltered
  5. washwashed by hexanes
  6. customto collect the off-white solid, which

Sources & evidence

ORD record
ord-34a6a127ef8646f4b597541a9a1a9507
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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