Triethylamine → HCID 178509869, compound

HRID 606440Notes

Reaction equation

HRID 606440 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9].[NH:13]1[CH:17]=[N:16][C:15]([SH:18])=[N:14]1.C(N(CC)CC)C>C(O)C>[NH:13]1[CH:17]=[N:16][C:15]([S:18][CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[C:8]#[N:9])=[N:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 135691673-(2-Chloroethoxy)benzonitrileHCID 178527894HCID 178527894, compound

Product 1

HCID 178509869HCID 178509869, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-[(2-chloroethyl)oxy]benzonitrile obtained in Reference Example 1 (11.3 g, 62.3 mmol), 1H-1,2,4-triazole-3-thiol (6.00 g, 59.3 mmol) and triethylamine (8.40 mL, 62.3 mmol) in ethanol (50 mL) was stirred at 80° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added to the residue. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated to give the title compound as a white powder (14.4 g, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and water
  2. additionwere added to the residue
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-93203ed7daf140af9c3d229af82b94b8
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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