Ethyl iodoacetate → 895571-94-5

HRID 901045Notes

Reaction equation

HRID 901045 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[H-].[Na+].[CH2:9]([O:11][C:12](=[O:15])[CH2:13]I)[CH3:10]>CN(C=O)C.O>[CH2:9]([O:11][C:12](=[O:15])[CH2:13][N:4]1[CH:5]=[N:6][C:2]([NH2:1])=[N:3]1)[CH3:10]

Participants

6

Reactant 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 178418311HCID 178418311, compound

Product 1

HCID 42643123895571-94-5

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

61.1 To a stirred mixture of 2.8 g 3-amino-1,2,4-triazole in 50 ml DMF, 1.57 g NaH were slowly added at 0° C. under an argon atmosphere. After 1 hr stirring at 0° C., 3.31 ml ethyliodoacetate were added. The reaction mixture was stirred at r.t. over night. The mixture was diluted with water and extracted with EtOAc and CH2Cl2/MeOH 9:1. The organic phase was dried (MgSO4), filtered and concentrated. The crude product was purified by chromatography on silica, using a gradient from CH2Cl2 to CH2Cl2/MeOH 9:1 and then crystallization from cyclohexane/EtOAc to give 750 mg (3-amino-[1,2,4]triazol-1-yl)-acetic acid ethyl ester as a white solid.

Workup

  1. additionwere slowly added at 0° C. under an argon atmosphere
  2. stirringThe reaction mixture was stirred at r.t. over night
  3. extractionextracted with EtOAc and CH2Cl2/MeOH 9:1
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography on silica
  8. customcrystallization from cyclohexane/EtOAc

Sources & evidence

ORD record
ord-07e78817063e4d9085e5cba8e9c4cbfa
Source dataset
uspto-grants-2008_04
Patent number
US07361672B2

Reaction notes

Loading…