4-Chloro-1,2-diaminobenzene → HCID 45381981, compound

HRID 1402939Notes

Reaction equation

HRID 1402939 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([O:20][C:21](=O)[CH:22]=2)=[O:19])=[CH:13][CH:12]=1>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:21]([CH2:22][CH:17]([C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=3)[C:18]([OH:20])=[O:19])[NH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 72634-Chloro-1,2-diaminobenzeneHCID 5859973-(4-Chlorophenyl)-2,5-furandione

Product 1

HCID 45381981HCID 45381981, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-1,2-phenylenediamine (285 mg) and 2-(4-chlorophenyl)maleic anhydride (420 mg) were dissolved in dichloromethane (4 ml) with heating. The dark solution was stirred at rt for 1 h. The solvent was removed in vacuo and the residue was dissolved in 1M HCl in acetic acid (4 ml). The solution was heated to reflux for 1 h, treated with charcoal, and filtered. From the filtrate the solvent was removed and the residue crystallised from acetone/ethyl acetate to give 3-(5-chloro-2-benzimidazolyl)-2-(4-chlorophenyl)propanoic acid HCl (130 mg) as light orange solid.

Workup

  1. temperaturewith heating
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 1M HCl in acetic acid (4 ml)
  4. temperatureThe solution was heated
  5. temperatureto reflux for 1 h
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. customFrom the filtrate the solvent was removed
  9. customthe residue crystallised from acetone/ethyl acetate

Sources & evidence

ORD record
ord-cf1ebd822b7243de961837964baf3232
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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