Acetic Acid → 2H-Tetrazole-5-carboxylic acid, 2-(3-chlorophenyl)-, ethyl ester

HRID 334028Notes

Reaction equation

HRID 334028 reaction equation
[C:1](O)(=O)[CH3:2].[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][N:13]=[C:14]([NH2:19])[CH2:15][O:16]CC)[CH:9]=[CH:10][CH:11]=1.[N:20]([O-])=O.[Na+].[OH2:24]>C1COCC1>[CH2:1]([O:24][C:15]([C:14]1[N:19]=[N:20][N:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[CH:7]=2)[N:13]=1)=[O:16])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 23668193Sodium NitriteHCID 86688257N'-(3-chlorophenyl)-2-ethoxyacetohydrazonamide

Product 1

HCID 5745342H-Tetrazole-5-carboxylic acid, 2-(3-chlorophenyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

12.0 mL (210 mmol) acetic acid was added to a solution of 12.0 g (52.7 mmol) N′-(3-chloro-phenyl)-2-ethoxyacetohydrazonamide in 120 mL THF. The mixture was heated to 85° C. and a solution of 4.36 g (63.2 mmol) sodium nitrite in 12 mL water was added over 4 h. After stirring for 1 h at 85° C., the mixture was cooled to RT. The solvent was evaporated. The residue was dissolved in EtOAc and extracted with aqueous sodium bicarbonate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography eluted with hexane/EtOAc (90:10).

Workup

  1. temperaturethe mixture was cooled to RT
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. extractionextracted with aqueous sodium bicarbonate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by column chromatography
  10. washeluted with hexane/EtOAc (90:10)

Sources & evidence

ORD record
ord-76622975f6764fc3953b86e7eaf3c459
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

Loading…