Hexane → HCID 135480553, compound

HRID 1491789Notes

Reaction equation

HRID 1491789 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[N:14]([Si](C)(C)C)=[N+:15]=[N-:16].CCCCCC>C(OCC)(=O)C>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:10](=[O:11])[NH:16][N:15]=[N:14]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 78378Azidotrimethylsilane

Product 1

HCID 135480553HCID 135480553, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
110 °C

Procedure

To 4-trifluoromethylphenyl isocyanate (2.89 ml, 20.2 mmol) was added 5.36 ml of azidotrimethylsilane (39.9 mmol), and the mixture was stirred at 110° C. for twenty-four hours. After cooling, the mixture was subjected to column chromatography using silicagel (eluate; ethyl acetate:hexane=1:1 to 2:1 to ethyl acetate) to collect a desired fraction to be concentrated. The crystals obtained were recrystallized from ethyl acetate-hexane to give 3.64 g of 1-(4-trifluoromethylphenyl)-5(1H,4H)-tetrazolone (78%) as colorless needles.

Workup

  1. temperatureAfter cooling
  2. customto collect a desired fraction
  3. concentrationto be concentrated
  4. customThe crystals obtained
  5. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-59919b65a0e643cd911731377d5801b4
Source dataset
uspto-grants-1994_12
Patent number
US05371101

Reaction notes

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