Sodium Azide → 1-(4-Benzyloxy-phenyl)-5-trifluoromethyl-1H-tetrazole

HRID 376269Notes

Reaction equation

HRID 376269 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16](Cl)[C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:16]([C:17]([F:20])([F:19])[F:18])=[N:24][N:23]=[N:22]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 21197258N-(4-Benzyloxy-phenyl)-2,2,2-trifluoro-acetimidoyl chloride

Product 1

HCID 211972511-(4-Benzyloxy-phenyl)-5-trifluoromethyl-1H-tetrazoleYield 68.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(4-Benzyloxy-phenyl)-(1-chloro-2,2,2-trifluoro-ethylidene)-amine (66 mmol) was added to a stirred flask of glacial acetic acid (250 ml) at 70° under nitrogen. After 4 min sodium azide (210 mmol) was added and heating was continued for 3 h. After cooling the mixture was filtered, the filtrate poured into water (750 ml) then extracted with dichloromethane (500 ml ×3). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. Purification by FCC using hexane-ethyl acetate (19:1) gave the title compound as a white solid (14.5 g).

Workup

  1. temperatureheating
  2. temperatureAfter cooling the mixture
  3. filtrationwas filtered
  4. additionthe filtrate poured into water (750 ml)
  5. extractionthen extracted with dichloromethane (500 ml ×3)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customPurification by FCC

Sources & evidence

ORD record
ord-e7c16257042f4a46be71acb48519d1b7
Source dataset
uspto-grants-2000_02
Patent number
US06020346

Reaction notes

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