Triethylamine → Ethyl 1-(2-fluorobenzyl)-1H-imidazo[2,1-c][1,2,4]triazole-3-carboxylate

HRID 1640337Notes

Reaction equation

HRID 1640337 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].C(S[C:22]1[NH:23][CH:24]=[CH:25][N:26]=1)C=C.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:26][CH:25]=[CH:24][N:23]2[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 552877472-Allylsulfanyl-1H-imidazoleHCID 58142732ethyl (2Z)-2-chloro-2-[(2-fluorophenyl)methylhydrazinylidene]acetate

Product 1

HCID 58142731Ethyl 1-(2-fluorobenzyl)-1H-imidazo[2,1-c][1,2,4]triazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl (2Z)-chloro[(2-fluorobenzyl)hydrazono]acetate (750 mg, 2.90 mmol) from example 2A, 2-allylthio-1H-imidazole [U.S. Pat. No. 3,574,593; Chem. Abstr. 75, 49078] (1.20 g, 7.25 mmol) and triethylamine (293 mg, 2.90 mmol) are dissolved in dioxane (10 ml) and heated under reflux for 4 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). 410 mg (41% of theory) of the desired product are obtained with 84% purity.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 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-88ef207e309d442ca261c1b95463e627
Source dataset
uspto-grants-2012_02
Patent number
US08114400B2

Reaction notes

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