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

HRID 1817228Notes

Reaction equation

HRID 1817228 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Cl.C(O[C:13](=N)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])C>C(O)C>[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:13]=1[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochloride

Product 1

HCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,2-phenylenediamine (1.0 eq) and ethyl 3-ethoxy-3-iminopropanoate hydrochloride (1.3 eq) in ethanol was stirred at 90° C. overnight. The reaction was cooled to room temperature and the solvent was removed in vacuo. Water and CH2Cl2 were added to the residue. The organic layer was separated, dried over Na2SO4 and the solvent removed. The solid recovered was used without purification. LC/MS m/z 205.2 (MH+), Rt 1.44 minutes.

Workup

  1. customthe solvent was removed in vacuo
  2. additionWater and CH2Cl2 were added to the residue
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed
  6. customThe solid recovered
  7. customwas used without purification

Sources & evidence

ORD record
ord-67204db9126d44dd8179955f2ae02db4
Source dataset
uspto-grants-2009_10
Patent number
US07598268B2

Reaction notes

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