Triethylamine → HCID 58142730, compound

HRID 1640338Notes

Reaction equation

HRID 1640338 reaction equation
Cl/[C:2](=[N:8]\[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])/[C:3]([O:5][CH2:6][CH3:7])=[O:4].CS[C:20]1[NH:24][N:23]=[CH:22][N:21]=1.C(N(CC)CC)C>O1CCOCC1>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][N:9]1[C:22]2=[N:23][N:24]=[CH:20][N:21]2[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5753783-Methylthio-4H-1,2,4-triazoleHCID 58142732ethyl (2Z)-2-chloro-2-[(2-fluorophenyl)methylhydrazinylidene]acetate

Product 1

HCID 58142730HCID 58142730, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl(2Z)-chloro[(2-fluorobenzyl)hydrazono]acetate (807 mg, 3.12 mmol) from example 2A, 5-(methylthio)-1H-1,2,4-triazole (359 mg, 3.12 mmol) and triethylamine (316 mg, 3.12 mmol) are dissolved in dioxane (5 ml) and heated under reflux for 6 h. This is followed by dilution with water and extraction with ethyl acetate. The organic phase is dried over sodium sulfate, and the crude product is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1). 124 mg (9.5% of theory) of the desired product are obtained with 69% purity.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 h
  3. extractionThis is followed by dilution with water and extraction with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe crude product is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1)

Sources & evidence

ORD record
ord-ced263f4cd55478fb73a13234c96c764
Source dataset
uspto-grants-2012_02
Patent number
US08114400B2

Reaction notes

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