Propargyl bromide → 5-benzhydrylthio-2-(2-propynyl)-2H-tetrazole

HRID 1649375Notes

Reaction equation

HRID 1649375 reaction equation
[CH:1]([S:14][C:15]1[NH:19][N:18]=[N:17][N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:27](Br)[C:28]#[CH:29]>O1CCCC1>[CH:1]([S:14][C:15]1[N:19]=[N:18][N:17]([CH2:29][C:28]#[CH:27])[N:16]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 178420440HCID 178420440, compound

Product 1

HCID 130511705-benzhydrylthio-2-(2-propynyl)-2H-tetrazoleYield 42.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-benzhydrylthio-1H-tetrazole (29 g) in tetrahydrofuran (145 ml) were added triethylamine (12.0 g) and 2-propynyl bromide (19.3 g) at room temperature. The resulting mixture was stirred for 2.5 hours at 40° to 45° C. The reaction mixture was filtered and the filtrate was evaporated. The residue was shaken with a mixture of ethyl acetate and water. The ethyl acetate layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated. The residual oil (27.7 g) was subjected to column chromatography on silica gel, and eluted with a mixture of n-hexane, chloroform and ethyl acetate (5.5:4.5:0.5), to give 5-benzhydrylthio-2-(2-propynyl)-2H-tetrazole (14.2 g), mp 85° to 86° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. stirringThe residue was shaken with a mixture of ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. washeluted with a mixture of n-hexane, chloroform and ethyl acetate (5.5:4.5:0.5)

Sources & evidence

ORD record
ord-0fd5410d3a6845f5af1fd3197aec7cbc
Source dataset
uspto-grants-1983_11
Patent number
US04416879

Reaction notes

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