Benzyl Chloride → 1-Benzyl-5-phenyl-1H-tetraazole

HRID 623230Notes

Reaction equation

HRID 623230 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([C:15]2[NH:19][N:18]=[N:17][N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na]>COCCO>[CH2:1]([N:19]1[C:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:16][N:17]=[N:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 178507078HCID 178507078, compound

Product 1

HCID 3079071-Benzyl-5-phenyl-1H-tetraazoleYield 92.5%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

Benzyl chloride (0.15 mole; 19.0 g), sodium 5-phenyltetrazole (0.165 mole; 27.4 g) and 2-methoxyethanol (100 ml) were heated at 100° C. for 3.5 hours). The mixture was cooled to precipitate NaCl. Water (250 ml) was added to the filtrate to precipitate a product which was filtered, washed with H2O (50 ml) and dried in-vacuo at 60° C. for four hours. The product weight was 32.8 g. (92.5 percent yield), m.p. 54°-67° C. Reported; 2-benzyl-5-phenyltetrazole, m.p. 65.5°-66° C. 1-benzyl-5-phenyltetrazole, m.p. 92.5°-93° C. Elemental analysis found: C, 71.57; H, 5.30; N, 21.39. Calculation for C14H 12N4 : C, 71.17; H, 5.12; N, 23.71. 13C NMR established a 3/1 isomer ratio for the 2-benzyl/1 -benzyl substitution products, respectively. The isomers are represented by the following structures; ##STR6##

Workup

  1. temperatureThe mixture was cooled
  2. customto precipitate NaCl
  3. additionWater (250 ml) was added to the filtrate
  4. customto precipitate a product which
  5. filtrationwas filtered
  6. washwashed with H2O (50 ml)
  7. customdried in-vacuo at 60° C. for four hours

Sources & evidence

ORD record
ord-832a299a7da84e658c17c689f71412d9
Source dataset
uspto-grants-1988_09
Patent number
US04774266

Reaction notes

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