Acetic Acid → HCID 178505771, compound

HRID 2297395Notes

Reaction equation

HRID 2297395 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[N-:11]=[N+:12]=[N-:13].[Na+].C(O)(=O)C.[OH-].[Na+]>CCOCC.C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([C:7]2[NH:13][N:12]=[N:11][N:8]=2)[CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 33557Sodium Azide2×HCID 936535-Chloro-2-fluorobenzonitrile

Product 1

HCID 178505771HCID 178505771, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-chloro-2-fluoro-benzonitrile (2.84 g, 0.01823 mol), butanol (15 mL), sodium azide (1.543 g, 0.0237 mol), acetic acid (1.36 mL, 0.0237 mol) was refluxed for 24 hours. The reaction mixture was cooled to room temperature, additional 1.543 g sodium azide added, and the reaction mixture refluxed for additional 24 hours. After cooling to room temperature, Et2O (100 mL) and 10% aqueous NaOH (200 mL) were added sequentially. The mixture was vigorously stirred. The aqueous layer was separated, cooled with ice-methanol bath (−15° C.) and acidified to pH 1 with conc. HCl. A gray solid precipitated. The solid was dried in vacuum at 50° C. to give 1.76 g (49%) of 5-(5-chloro-2-fluoro-phenyl)-1H-tetrazole: mp partial melt at 110° C., complete melting at 124° C.);

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturethe reaction mixture refluxed for additional 24 hours
  3. temperatureAfter cooling to room temperature
  4. customThe aqueous layer was separated
  5. temperaturecooled with ice-methanol bath (−15° C.)
  6. customA gray solid precipitated
  7. customThe solid was dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-7c2eb41e727f4587aebb88b6dc5c0b24
Source dataset
uspto-grants-2002_12
Patent number
US06492363B2

Reaction notes

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