Methanesulfonic Acid → 3-(4-Bromophenyl)-4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazole

HRID 1401248Notes

Reaction equation

HRID 1401248 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[N:10][N:9]=2)=[CH:4][CH:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.CS(O)(=O)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][O:13]3)[CH:11]=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 178419362HCID 178419362, compound

Product 1

HCID 666076483-(4-Bromophenyl)-4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazoleYield 248.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-Bromophenyl)-4H-1,2,4-triazole (14.1 g, 62.9 mmol), 3,4-dihydro-2H-pyran (10.59 mmol) and methanesulfonic acid (1.19 g, 6.29 mmol) in tetrahydrofuran (150 mL) was heated at 75° C. for 2 h. The solution was condensed and partitioned between sodium bicarbonate solution and ethyl acetate (3×), the organics dried over magnesium sulfate, filtered and solvent removed under reduced pressure. The solid was triturated with 10% ethyl acetate in hexanes to afford the title compound (8.1 g, 26.3 mmol, 70% yield). MS (ESI) m/z 308.4 [M]+, 310.5 [M+2]+.

Workup

  1. customcondensed
  2. custompartitioned between sodium bicarbonate solution and ethyl acetate (3×)
  3. dry with materialthe organics dried over magnesium sulfate
  4. filtrationfiltered
  5. customsolvent removed under reduced pressure
  6. customThe solid was triturated with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-be217386f2284bdbae07b0a544029b73
Source dataset
uspto-grants-2014_12
Patent number
US08907087B2

Reaction notes

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