Azidotrimethylsilane → 1-[4-(4-fluorophenylmethoxy)-2-fluorophenyl]-1,4-dihydro-5H-tetrazol-5-one

HRID 257368Notes

Reaction equation

HRID 257368 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[C:12]([F:19])[CH:11]=2)=[CH:4][CH:3]=1.C[Si]([N:24]=[N+:25]=[N-:26])(C)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:17](=[O:18])[NH:26][N:25]=[N:24]3)=[C:12]([F:19])[CH:11]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 189810564-(4-Fluorophenylmethoxy)-2-fluorophenyl isocyanate

Product 1

HCID 1357033291-[4-(4-fluorophenylmethoxy)-2-fluorophenyl]-1,4-dihydro-5H-tetrazol-5-oneYield 98.4%

Procedure

A mixture of 7.10 g (0.027 mole) of 4-(4-fluorophenylmethoxy)-2-fluorophenyl isocyanate and 7.0 g (0.060 mole) of trimethylsilyl azide was heated at reflux for approximately seventeen hours. The solution was then allowed to cool to room temperature before being poured over ice. A solid formed and was recovered by filtration. The solid was dried, leaving 8.08 g of 1-[4-(4-fluorophenylmethoxy)-2-fluorophenyl]-1,4-dihydro-5H-tetrazol-5-one, m.p. 171°-172° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately seventeen hours
  3. additionbefore being poured over ice
  4. customA solid formed
  5. filtrationwas recovered by filtration
  6. customThe solid was dried

Sources & evidence

ORD record
ord-e6e29e9a3fb9485ea0740e07d55e9da9
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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