Ammonium Chloride → HCID 58541950, compound

HRID 1966732Notes

Reaction equation

HRID 1966732 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]#[N:12])=[N:8][C:4]=2[CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:17]([CH3:18])([CH3:19])[CH3:20])[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]3[N:23]=[N:24][NH:25][N:12]=3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 58542011HCID 58542011, compound

Product 1

HCID 58541950HCID 58541950, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
110 °C

Procedure

To a round bottom flask is added 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzonitrile (200 mg, 0.565 mmol) in DMF (3 mL), follow by the addition of NaN3 (48 mmol, 0.738 mmol) and NH4Cl (39 mg, 0.729 mmol). The reaction mixture is stirred at 110° C. for 48 hours. The reaction mixture is diluted with EtOAc/water. The organic layer is separated, washed with water then brine, dried with Na2SO4, filtered and concentrated to afford 5-bromo-1-tert-butyl-2-[2-(2H-tetrazol-5-yl)-phenyl]-1H-benzimidazole (190 mg, 85%) as a solid product. LCMS (ESMS): m/z 397.49, 399.40 (M++1)

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialbrine, dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-059443a57bfa40d4abb38bf2edfe1a4d
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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