Ethyl orthoformate → HCID 67518254, compound

HRID 2173400Notes

Reaction equation

HRID 2173400 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([S:12][CH3:13])[CH:3]=1.[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(O)=O>[CH3:13][S:12][C:4]1[CH:3]=[C:2]([N:1]2[CH:14]=[N:26][N:25]=[N:24]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 67516005HCID 67516005, compound

Product 1

HCID 67518254HCID 67518254, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of [4-amino-2-(methylsulfanyl)phenyl]acetic acid (200 mg, 1 mmol) and triethyl orthoformate (451 mg, 3 mmol) in 10 mL of HOAc was added sodium azide (99 mg, 1.5 mmol), and the mixture was heated to 100° C. for 3 hours. The reaction mixture was cooled to ambient temperature. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative TLC to give [2-(methylsulfanyl)-4-(1H-tetrazol-1-yl)phenyl]acetic acid.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-f531af7bec7142d9beb32f39992e65d9
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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