Ethyl orthoformate → HCID 57851246, compound

HRID 217334Notes

Reaction equation

HRID 217334 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-ace8d01dbd8a42f9a9b280f5df3db20a
Source dataset
uspto-grants-2012_06
Patent number
US08193368B2

Reaction notes

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