Sodium Azide → 2-[4-(Diphenylmethoxy)phenyl]-1-cyclohexyl-5-(1H-tetrazol-5-yl)-1H-benzimidazole

HRID 392961Notes

Reaction equation

HRID 392961 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[N-:5]=[N+:6]=[N-:7].[Na+].[N-]=[N+]=[N-].[Al+3].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[C:19]1([CH:25]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[N:37]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[C:36]4[CH:44]=[CH:45][C:46]([C:48]#[N:49])=[CH:47][C:35]=4[N:34]=3)=[CH:29][CH:28]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:50]1([CH:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[N:37]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[C:36]4[CH:44]=[CH:45][C:46]([C:48]5[NH:49][N:7]=[N:6][N:5]=5)=[CH:47][C:35]=4[N:34]=3)=[CH:29][CH:28]=2)[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

5

Reactant 4

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 21652180Aluminum azideHCID 226607932-[4-(Diphenylmethoxy)phenyl]-1-cyclohexyl-1H-benzimidazole-5-carbonitrile

Product 1

HCID 1784203842-[4-(Diphenylmethoxy)phenyl]-1-cyclohexyl-5-(1H-tetrazol-5-yl)-1H-benzimidazoleYield 20.6%

Procedure

Aluminum trichloride (33 mg, 0.247 mmol) was added to ice cold THF (4 mL). Sodium azide (48 mg, 0.744 mmol) was added and the resulting mixture was stirred under reflux for 30 min to complete the formation of the aluminum azide. Compound 8 (100 mg, 0.206 mmol) was added and the mixture stirred under reflux for 18 h. The reaction mixture was poured into ice cold dilute HCl to precipitate a solid. The solid was dissolved in DMF (2 mL) and the solution applied to a Shimadzu Prep HPLC. The product containing fractions were combined. Removal of the methanol resulted in the precipitation of 9 as a colorless solid (22.3 mg, 20.6% yield). ESI-MS m/e 527 (M=1). 1H NMR (DMSO) δ 8.33 (s, 1H), 8.20 (d, 1H, J=8.6 Hz), 8.0 (1H, d, J=7.41 Hz), 7.63 (d, 2H, J=8.7 Hz), 7.55 (d, 4H, J=7.2 Hz), 7.41-7.37 (m, 4H), 7.34-7.26 (m, 4). 6.72 (s, 1H), 4.34-4.27 (m, 1H), 2.36-2.23 (m, 2H), 1.97-1.83 (m, 4H), 1.66-1.62 (m, 1H), 1.43-1.21 (m. 3H).

Workup

  1. temperatureunder reflux for 30 min
  2. stirringthe mixture stirred
  3. temperatureunder reflux for 18 h
  4. additionThe reaction mixture was poured into ice cold dilute HCl
  5. customto precipitate a solid
  6. dissolutionThe solid was dissolved in DMF (2 mL)
  7. additionThe product containing fractions
  8. customRemoval of the methanol

Sources & evidence

ORD record
ord-7c73f6c2d1f541cebf85bdd1129ee807
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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