Hydrochloric Acid → 5-[3,4-Bis(benzyloxy)-5-nitrophenyl]-2H-tetrazole

HRID 1920079Notes

Reaction equation

HRID 1920079 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([N+:25]([O-:27])=[O:26])[C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12]2[N:28]=[N:29][NH:30][N:13]=2)[CH:14]=[C:15]([N+:25]([O-:27])=[O:26])[C:16]=1[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 670369943,4-Bis(benzyloxy)-5-nitrobenzonitrile

Product 1

HCID 670370545-[3,4-Bis(benzyloxy)-5-nitrophenyl]-2H-tetrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3,4-bis-benzyloxy-5-nitro-benzonitrile (0.54 g, 1.50 mmol), sodium azide (0.15 g, 2.25 mmol) and ammonium chloride (0.12 g, 2.25 mmol) in dimethylformamide (3 mL) was stirred at 85° C. for 20 hours. After cooling to room temperature, the reaction mixture was poured onto water (30 mL) and acidified with dilute hydrochloric acid. The resulting precipitate was collected, washed with water and dried to yield 5-(3,4-bis-benzyloxy-5-nitro-phenyl)-2H-tetrazole, 0.53 g (87%).

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was poured onto water (30 mL)
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8c299985d8154f9ea1893e63d504ead0
Source dataset
uspto-grants-2012_05
Patent number
US08168793B2

Reaction notes

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