Ammonium Chloride → HCID 178525021, compound

HRID 1639536Notes

Reaction equation

HRID 1639536 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22]([C:25]2[NH:29][N:28]=[N:27][N:26]=2)=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18974028Benzyl 2-benzyloxy-5-cyanobenzoate

Product 1

HCID 178525021HCID 178525021, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 436 mg (1.27 mmol) of benzyl 2-benzyloxy-5-cyanobenzoate, 91 mg (1.40 mmol) of sodium azide, and 68 mg (1.27 mmol) of ammonium chloride in 5 mL of DMF is heated at 120° C. for 24 hrs. The DMF was removed by rotoevaporation, the residue is taken up in water, and acidified. The white precipitate is collected by filtration and dried to give 500 mg of unpurified benzyl 2-benzyloxy-5-(1H-tetrazol-5-yl)benzoate, which is treated with 28% aqueous ammonium hydroxide in 5 mL of MeOH at 85° C. for 72 hrs. The reaction mixture was concentrated, taken up in water, and then acidified. Filtration of the precipitate gives 400 mg (1.04 mmol, 82% yield) of 2-benzyloxy-5-(1H-tetrazol-5-yl)benzamide.

Workup

  1. customThe DMF was removed by rotoevaporation
  2. filtrationThe white precipitate is collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-dc3f10dcd0af4f3da12dd460bb2199b3
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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