p-Toluenesulfonic acid → 1-[Bis-(3-benzyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole

HRID 1685643Notes

Reaction equation

HRID 1685643 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:20]=2)O)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:35]1[CH:39]=[N:38][CH:37]=[N:36]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:20]=2)[N:35]2[CH:39]=[N:38][CH:37]=[N:36]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 92571H-1,2,4-TriazoleHCID 58734013Bis-(3-benzyloxy-4-methoxyphenyl)methanol

Product 1

HCID 587340101-[Bis-(3-benzyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazoleYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bis-(3-benzyloxy-4-methoxyphenyl)methanol (1.60 g, 3.50 mmol), 1,2,4-triazole (0.48 g, 6.95 mmol) and p-TSA (160 mg) dissolved/suspended in toluene (230 mL) were heated at reflux with a Dean-Stark separator for 24 h. The reaction mixture was allowed to cool, and the solvent was removed in vacuo. The resulting residue was dissolved in EtOAc (100 mL) and the organic layer was washed with H2O (3×100 mL), dried (MgSO4) and the solvent was removed in vacuo. The crude product was purified using Flashmaster II (EtOAc/Hexane) to give the title compound (1.51 g, 84%, mp 96-99° C.) as a yellow oil which solidified after standing for a prolonged period; δH (400 MHz, CDCl3) 7.95 (1H, s, NCHN), 7.67 (1H, s, NCHN), 7.34-7.24 (10H, m, ArH), 6.81 (2H, d, J=8.4, ArH), 6.58-6.48 (5H, m, ArH), 5.00 (4H, s, 2×CH2), 3.84 (6H, s, 2×CH3); δC (100 MHz, CDCl3) 152.3 (CH), 149.9 (2×C), 148.2 (2×C), 143.4 (CH), 136.7 (2×C), 130.5 (2×C), 128.7 (4×CH), 128.1 (2×CH), 127.5 (4×CH), 121.1 (2×CH), 114.1 (2×CH), 118.8 (2×CH), 71.2 (2×CH2), 67.4 (CH), 56.4 (2×CH3); LRMS (FAB+) 507.2 (M+, 20%), 439.2 (100), 349.2 (15), 257.2 (15), 91.1 (35); HRMS (FAB+) Found 507.2159, C31H29N3O4 requires 507.2158; Found: C, 73.00%; H, 5.73%; N, 8.31%, C31H29N3O4 requires: C, 73.35%; H, 5.76%; N, 8.28%.

Workup

  1. temperaturewere heated
  2. temperatureat reflux with a Dean-Stark separator for 24 h
  3. temperatureto cool
  4. customthe solvent was removed in vacuo
  5. dissolutionThe resulting residue was dissolved in EtOAc (100 mL)
  6. washthe organic layer was washed with H2O (3×100 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed in vacuo
  9. customThe crude product was purified

Sources & evidence

ORD record
ord-ff6b28bd8e194209863a57d80af78e84
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

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