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

HRID 1488403Notes

Reaction equation

HRID 1488403 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-db775b4d222f45d492d5e6b0575a1fd1
Source dataset
uspto-grants-1997_10
Patent number
US05674810

Reaction notes

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