Sodium Hydroxide → HCID 178418490, compound

HRID 1629

Reaction equation

HRID 1629 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N:21]=[N+:22]=[N-:23])(C)C.C([Sn](=O)CCCC)CCC.[OH-].[Na+]>C1(C)C=CC=CC=1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]2[NH:23][N:22]=[N:21][N:16]=2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 27779534-Phenoxyphenylacetonitrile

Product 1

HCID 178418490HCID 178418490, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-phenoxyphenylacetonitrile (1.16 g) in anhydrous toluene (30 ml) was added trimethylsilylazide (1.1 ml) and dibutyltin oxide (0.19 g). The mixture was heated to reflux for 19 hours then allowed to cool to room temperature. The reaction mixture was then added to 1M sodium hydroxide (100 ml) and washed with diethyl ether (3×50 ml). The aqueous layer was acidified with concentrated hydrochloric acid (30 ml) then washed with 5:1 ethyl acetate/tetrahydrofuran (60 ml) and ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to give 5-(4-phenoxyphenylmethyl)-1H-tetrazole as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 19 hours
  3. washwashed with diethyl ether (3×50 ml)
  4. washthen washed with 5:1 ethyl acetate/tetrahydrofuran (60 ml) and ethyl acetate (2×50 ml)
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-25fc14e42f424677aa73d3c6c5b9ae9d
Source dataset
uspto-grants-1998_03
Patent number
US05726195

Linked notes

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