Iodoethane → HCID 69642563, compound

HRID 1828090Notes

Reaction equation

HRID 1828090 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([OH:18])[C:6]1[N:10]=[C:9]([CH3:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1)[CH3:2].[CH2:20](I)[CH3:21]>C1(C)C=CC=CC=1.[Ag-]=O>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:18][CH2:20][CH3:21])[C:6]1[N:10]=[C:9]([CH3:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 69642321HCID 69642321, compound

Product 1

HCID 69642563HCID 69642563, compound

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of (RS)-hydroxy-(5-methyl-1-phenyl-1H-[1,2,4]triazol-3-yl)-acetic acid ethyl ester (1.12 g) at r.t. in toluene (30 ml) under an argon atmosphere were added silver (I) oxide (2.99 g) and ethyl iodide (1.74 ml). The mixture was heated to reflux and stirring was continued for 16 h. The solids were filtered off and washed with EtOAc. The filtrate was concentrated. The product was isolated by chromatography (silica gel, gradient cyclohexane=>EtOAc) to give (RS)-ethoxy-(5-methyl-1-phenyl-1H-[1,2,4]triazol-3-yl)-acetic acid ethyl ester (0.87 g) as orange oil. MS 290.1 ([M+H]+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationThe solids were filtered off
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. customThe product was isolated by chromatography (silica gel, gradient cyclohexane=>EtOAc)

Sources & evidence

ORD record
ord-6885a2238fbb4601895d28aedf147aa1
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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