Triethylamine → HCID 178521527, compound

HRID 606449Notes

Reaction equation

HRID 606449 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([SH:6])=[N:2]1.I[CH2:8][CH2:9][OH:10].C(N(CC)CC)C>C(O)C>[NH:1]1[CH:5]=[N:4][C:3]([S:6][CH2:8][CH2:9][OH:10])=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12225IodoethanolHCID 178527894HCID 178527894, compound

Product 1

HCID 178521527HCID 178521527, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1H-1,2,4-triazole-3-thiol (14.7 g, 145 mmol), 2-iodoethanol (25.0 g, 145 mmol) and triethylamine (14.7 g, 145 mmol) in ethanol (400 mL) was stirred at 80° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was acidified with water and 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The obtained oil was purified by silica gel column chromatography (10%-100% ethyl acetate/hexane) to give the title compound as a colorless oil (7.30 g, 35%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained oil was purified by silica gel column chromatography (10%-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-062d5293625f490eb1a0a19b3947a226
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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