Acetonitrile → HCID 22380285, compound

HRID 1594047Notes

Reaction equation

HRID 1594047 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13]O)=[N:11][CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[C:19](#[N:21])C.C(N(CC)CC)C>ClCCl.[C-]#N.C([N+](CC)(CC)CC)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][C:19]#[N:21])=[N:11][CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 22379921HCID 22379921, compound

Product 1

HCID 22380285HCID 22380285, compound

Reagents, catalysts & solvents 3

HCID 3014735Tetraethylammonium cyanideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Fluorophenyl)-5-hydroxymethyl-1,2,4-triazole (1.7 g) is treated with thionyl chloride (10 mL) in dichloromethane (20 mL) at room temperature overnight. The solvent is then removed. To the residue is added acetonitrile (20 mL), tetraethylammonium cyanide (2.75 g, 17.6 mmol), and triethylamine (2.5 mL, 17.6 mmol). The mixture is stirred at room temperature for 2 h. The mixture is diluted with ethyl acetate, washed with aqueous bicarbonate, and then with saturated aqueous sodium chloride, dried (Na2SO4), concentrated and the residue purified by silica gel chromatography to give crude 1-(3-Fluorophenyl)-5-cyanomethyl-1,2,4-triazole. 1H NMR (CDCl3): δ 8.06 (s, 1H), 7.52-7.62 (m, 1H), 7.20-7.30 (m, 3H), 3.98 (s, 2H). LCMS 203.0 (MH+), 201.2 (MH−).

Workup

  1. customThe solvent is then removed
  2. washwashed with aqueous bicarbonate
  3. dry with materialwith saturated aqueous sodium chloride, dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-d8c66eb6ec854055a2ff225272c55217
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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