Ethyl orthoformate → HCID 57851246, compound

HRID 84733Notes

Reaction equation

HRID 84733 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH3+:16])[CH:5]=[C:6]([C:8](=[O:15])[NH:9][CH:10]([CH3:14])[CH2:11][O:12][CH3:13])[CH:7]=1.[N-:17]=[N+:18]=[N-:19].[Na+].[CH:21](OCC)(OCC)OCC>CC(O)=O>[I:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([N:16]2[CH:21]=[N:19][N:18]=[N:17]2)[CH:3]=1)[C:8]([NH:9][CH:10]([CH3:14])[CH2:11][O:12][CH3:13])=[O:15]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 866173873-Iodo-5-(2-methoxy-1-methyl-ethylcarbamoyl)-phenyl-ammonium

Product 1

HCID 57851246HCID 57851246, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-Iodo-5-(2-methoxy-1-methyl-ethylcarbamoyl)-phenyl-ammonium (7.47 g, 22.4 mmol) and NaN3 (2.68 g, 41.2 mmol) in AcOH (100 mL) was added HC(OEt)3 (18.3 mL, 110 mmol) at room temperature. The reaction mixture was brought to reflux for 4 hours, then cooled to room temperature. The solvent was removed in vacuo and the residue was purified by silica-gel chromatography to give 3-Iodo-N-(2-methoxy-1-methyl-ethyl)-5-tetrazol-1-yl-benzamide as a white solid (6.30 g, 72%). MS (M+H)=388.

Workup

  1. temperatureto reflux for 4 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-e4a01e9d7ee34e65a8e8dffaa4f9895c
Source dataset
uspto-grants-2014_09
Patent number
US08846945B2

Reaction notes

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