Acetic Acid → HCID 178505771, compound

HRID 382262Notes

Reaction equation

HRID 382262 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-64cbfb41d9b24c38bfd399fbb7ab7048
Source dataset
uspto-grants-2001_10
Patent number
US06310060B1

Reaction notes

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