Ethyl orthoformate → HCID 67517423, compound

HRID 2173408Notes

Reaction equation

HRID 2173408 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([CH3:12])[CH:3]=1.[CH:13](OCC)(OCC)OCC.[N-:23]=[N+:24]=[N-:25].[Na+]>C(O)(=O)C>[CH3:12][C:4]1[CH:3]=[C:2]([N:1]2[CH:13]=[N:25][N:24]=[N:23]2)[CH:7]=[CH:6][C:5]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 18794287HCID 18794287, compound

Product 1

HCID 67517423HCID 67517423, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (4-amino-2-methylphenyl)acetic acid (0.10 g, 0.61 mmol) and triethyl orthoformate (0.16 ml, 0.97 mmol) in acetic acid (1 ml) was added sodium azide (0.059 g, 0.91 mmol). The resulting mixture was heated to reflux for 4 hours. The mixture was poured into ice water and the resulting solid collected by filtration and dried, under vacuum to provide [2-methyl-4-(1H-tetrazol-1-yl)phenyl]acetic acid. LC-MS (IE, m/z): 219 [M+1]+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe resulting solid collected by filtration
  4. customdried, under vacuum

Sources & evidence

ORD record
ord-2505ddd6daca42d9a77351bf6bd025d7
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…