Azidotrimethylsilane → HCID 136098655, compound

HRID 569695Notes

Reaction equation

HRID 569695 reaction equation
[F:1][C:2]1[C:15]([N:16]=[C:17]=[O:18])=[CH:14][C:5]2[N:6]([CH2:11][CH2:12][CH3:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N:19]([Si](C)(C)C)=[N+:20]=[N-:21]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:15]([N:16]2[C:17](=[O:18])[NH:21][N:20]=[N:19]2)=[CH:14][C:5]2[N:6]([CH2:11][CH2:12][CH3:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 14099380HCID 14099380, compound

Product 1

HCID 136098655HCID 136098655, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a dry nitrogen atmosphere, 4.3 grams of 7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one-6yl isocyanate and 4.3 g (0.037 mole) of azidotrimethylsilane were heated at reflux for approximately 18 hours. The mixture was allowed to cool to room temperature and was diluted with toluene. This mixture was poured into ice-water forming a precipitate. The precipitate was collected by vaccum filtration, and the filter cake was rinsed first with water followed by diethyl ether. The filter cake was dissolved in acetone, and the organic solution was dried over anhydrous magnesium sulfate. This mixture was filtered, and the filtrate was evaporated under reduced pressure to yield 2.2 grams of 1-(7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one-6-yl)-1,4-dihydro-5H-tetrazol-5 one as a solid m.p. 145°-148° C.

Workup

  1. temperatureat reflux for approximately 18 hours
  2. filtrationThe precipitate was collected by vaccum filtration
  3. washthe filter cake was rinsed first with water
  4. dissolutionThe filter cake was dissolved in acetone
  5. dry with materialthe organic solution was dried over anhydrous magnesium sulfate
  6. filtrationThis mixture was filtered
  7. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b247c400072345549c7af6b9178c95c3
Source dataset
uspto-grants-1988_03
Patent number
US04734124

Reaction notes

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