Sodium Hydroxide → HCID 22001320, compound

HRID 325241Notes

Reaction equation

HRID 325241 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([O-:20])=[O:19])=[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])[CH:15]=2)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([N:8]1[C:12]([CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])[CH:15]=2)=[N:11][N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22001464HCID 22001464, compound

Product 1

HCID 22001320HCID 22001320, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50 mL round-bottom flask was charged with 4-(l-benzyltetrazol-5-ylmethyi)-2-(2-methylphenyl)benzoate (A) (205.8 mg, 0.52 mmol) and ethanol (10 mL). 4 N sodium hydroxide (1.1 mL, 4.16 mmol) was added. The reaction was refluxed for 2 h and then cooled. The solvent was removed under vacuum and then diluted with water. The reaction was extracted with Et2O (3×10 mL). The pH of the aqueous layer was adjusted to 2 with 1 M H3PO4. The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (10 mL), dried over MgSO4, filtered and concentrated under vacuum. Yield: 205.1 mg, white solid. 1H NMR (δ, CDCl3): 8.0 (2H), 7.0-7.4 (10H), 5.7 (2H), 4.3 (2H), 2.0 (3H).

Workup

  1. temperatureThe reaction was refluxed for 2 h
  2. temperaturecooled
  3. customThe solvent was removed under vacuum
  4. additiondiluted with water
  5. extractionThe reaction was extracted with Et2O (3×10 mL)
  6. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  7. washThe combined organic layers were washed with brine (10 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-52e70556d1964d58ae951267f6561e80
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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