Hydrochloric Acid → HCID 178418666, compound

HRID 4944

Reaction equation

HRID 4944 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N(CC)CC)C.[N-:25]=[N+:26]=[N-:27].[Na+].Cl>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[NH:27][N:26]=[N:25][N:14]=2)=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 5613714-Benzyloxybenzonitrile

Product 1

HCID 178418666HCID 178418666, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 285 g of the nitrile, 262.5 g triethylamine hydrochloride and 124 g of sodium azide in 1.5 L of DMF under nitrogen was stirred under reflux for 18 hrs. The reaction mixture was cooled to room temperature, poured into 4 L of cold water and acidified with 3N HCl. The resulting white solid was collected, washed with water and dried at 60° C. in vacuo for 48 hrs to give 337 g of 5-(4-benzyloxyphenyl)tetrazole.

Workup

  1. temperatureunder reflux for 18 hrs
  2. customThe resulting white solid was collected
  3. washwashed with water
  4. customdried at 60° C. in vacuo for 48 hrs

Sources & evidence

ORD record
ord-da4ba2e333534753ac71b51a2ea124e5
Source dataset
uspto-grants-1993_09
Patent number
US05242924

Linked notes

Loading…