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

HRID 2377824Notes

Reaction equation

HRID 2377824 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 equivalent) and ethyl 3-ethoxy-3-iminopropanoate hydrochloride (1.3 equivalents) 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-ed685717f7c34f8dad06093381c5e550
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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