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

HRID 1169988Notes

Reaction equation

HRID 1169988 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-6df831b7c5014e5b811de6349cc3d5a4
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

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