Azidotrimethylsilane → 1-(2-chloro-4-fluoro-5-methoxyphenyl)-1,4-dihydro-5H-tetrazol-5-one

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N:11]=[C:12]=[O:13].C[Si]([N:18]=[N+:19]=[N-:20])(C)C>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N:11]1[C:12](=[O:13])[NH:20][N:19]=[N:18]1

Participants

Reactant 2

HCID 78378Azidotrimethylsilane

HCID 198828332-Chloro-4-fluoro-5-methoxyphenyl isocyanate

Product 1

HCID 1361601361-(2-chloro-4-fluoro-5-methoxyphenyl)-1,4-dihydro-5H-tetrazol-5-oneYield 76.7%

Procedure

In the manner of Example 2, Step E, the reaction of 3.2 g (0.016 mole) of 2-chloro-4-fluoro-5-methoxyphenyl isocyanate with 3.2 g (0.028 mole) of trimethylsilyl azide produced 3.0 g of 1-(2-chloro-4-fluoro-5-methoxyphenyl)-1,4-dihydro-5H-tetrazol-5-one.

Sources & evidence

ORD record: ord-abe9d8d67988493fbf7c2091574f4235
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05136868

Reaction notes

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