Acetic Acid → HCID 178505613, compound

HRID 1656141Notes

Reaction equation

HRID 1656141 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(O)CCC.[N-:15]=[N+:16]=[N-:17].[Na+].C(O)(=O)C>C(OCC)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]1[NH:17][N:16]=[N:15][N:5]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 2631-ButanolHCID 33557Sodium Azide2×HCID 678552-Fluorobenzonitrile

Product 1

HCID 178505613HCID 178505613, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The 5-(2-fluorophenyl)-1H-tetrazole starting material was prepared as follows. A 3-necked 500 ml round-bottom flask was charged with 2-fluorobenzonitrile (48.4 g, 0.4 mol), n-butanol (160 ml), NaN3 (34.3 g, 0.528 mol) and glacial acetic acid (31.7 g, 0.528 mol). The mixture was warmed to a mild reflux for 24 h under nitrogen behind a safety shield. After the mixture had cooled to room temperature, it was again charged with NaN3 (34.3 g, 0.528 mol) and glacial acetic acid (31.7 g, 0.528 mol). The mixture was warmed to a mild reflux for an additional 24 h under nitrogen, cooled and then diluted with diethyl ether (320 ml). This organic mixture was extracted with 2N NaOH (4×100 ml) and the combined ice-cold basic extracts were carefully acidified to pH 1 with concentrated hydrochloric acid. The product was isolated as a light gray solid (45.2 g, 68.9%) after drying under vacuum at 60° C., mp 160.5°-162° C. [lit. mp 160°-162° C.; George, E. F. and Riddell, W. D., U.S. Pat. No. 3,865,570 (Feb. 13, 1973)]. There was obtained a second crop of product (1.0 g, 1.5%). A 1.0 g sample of this material was crystallized from water to produce a white solid, mp 162.5°-163.5° C.

Workup

  1. temperatureThe mixture was warmed to
  2. temperaturea mild reflux for 24 h under nitrogen behind a safety shield
  3. temperatureThe mixture was warmed to
  4. temperaturea mild reflux for an additional 24 h under nitrogen
  5. temperaturecooled
  6. extractionThis organic mixture was extracted with 2N NaOH (4×100 ml)

Sources & evidence

ORD record
ord-0f0982e146b745999b94e91e6f6549d6
Source dataset
uspto-grants-1993_10
Patent number
US05252753

Reaction notes

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