O-Phenylenediamine → ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate

HRID 1771119Notes

Reaction equation

HRID 1771119 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH2:9]([O:11][C:12](=[O:19])[CH2:13][C:14](OCC)=N)[CH3:10]>C(O)(=O)C>[CH2:9]([O:11][C:12](=[O:19])[CH2:13][C:14]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1)[CH3:10]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 75346Propanoic acid, 3-ethoxy-3-imino-, ethyl ester

Product 1

HCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

54 g o-phenylenediamine (0.5 mol), 300 mL glacial acetic acid and 98 g 3-ethoxy-3-imino propionic acid ethyl ester (0.5 mol) were stirred at refluxing for 2 hours. After concentration under reduced pressure, the residual solution was poured into ice water and a solid was isolated. After sucking filtration, washing with water and a little amount of ethanol, and drying, 83 g off-white solid was obtained. Yield: 82%, MS: 205 (M+1).

Workup

  1. temperatureat refluxing for 2 hours
  2. concentrationAfter concentration under reduced pressure
  3. additionthe residual solution was poured into ice water
  4. customa solid was isolated
  5. filtrationfiltration
  6. washwashing with water
  7. dry with materiala little amount of ethanol, and drying

Sources & evidence

ORD record
ord-ca3ef0decc6c4c3a950a7e68c2074433
Source dataset
uspto-grants-2016_02
Patent number
US09249106B2

Reaction notes

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