2-Butyl-1-[[4-[2-(2-trityltetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole → HCID 178441449, compound

HRID 1681376Notes

Reaction equation

HRID 1681376 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:24]=[N:25][N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:27]=3)=[CH:13][CH:12]=2)[C:8]2[CH:47]=[CH:48][CH:49]=[CH:50][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]>Cl.O1CCOCC1.O>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]2[CH:47]=[CH:48][CH:49]=[CH:50][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 42865832-Butyl-1-[[4-[2-(2-trityltetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole

Product 1

HCID 178441449HCID 178441449, compoundYield 37.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Butyl-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]benzimidazole (E) (400 mg) was dissolved in an 8M solution of hydrogen chloride in dioxan (5 ml) and water (0.5 ml) was added. The solution was allowed to stand for 1.5 hours and then volatile material was removed by evaporation. The residue was partitioned between sodium hydrogen carbonate solution (10 ml) and ether (10 ml). The aqueous phase was separated, washed with ether (3×10 ml) and acidified to pH4 with 20% aqueous citric acid. The precipitated solid was collected and recrystallised from ethyl acetate to give 2-butyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]benzimidazole (94 mg), as white crystals, m.p. 230°-232° C.; NMR (d6 -DMSO): 0.88(t,3H), 1.35(m,2H), 1.7(m,2H), 2.8(t,2H), 5.5(s,2H), 7.0(s,4H), 7.15(m,2H), 7.4-7.7 (complex, 6H); mass spectrum (-ve FAB, DMSO/NBA): 407 (M-H)-, 379; microanalysis found: C,73.7; H,6.2; N,20.8; C25H24N6 requires: C,73.5; H,5.9; N,20.6%.

Workup

  1. additionwas added
  2. customvolatile material was removed by evaporation
  3. customThe residue was partitioned between sodium hydrogen carbonate solution (10 ml) and ether (10 ml)
  4. customThe aqueous phase was separated
  5. washwashed with ether (3×10 ml)
  6. customThe precipitated solid was collected
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-5a9756a6b6234865805fbdc7dc632603
Source dataset
uspto-grants-1992_12
Patent number
US05171748

Reaction notes

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