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

HRID 2225395Notes

Reaction equation

HRID 2225395 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-92677cfa9d764992bc9b645091c59335
Source dataset
uspto-grants-1994_09
Patent number
US05344812

Reaction notes

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