4-Iodobenzene-1,2-diamine → HCID 45381313, compound

HRID 1402815Notes

Reaction equation

HRID 1402815 reaction equation
[I: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]([CH:17]2[CH2:23][C:22](=O)[O:21][C:19](=[O:20])[CH2:18]2)=[C:13]([CH3:25])[CH:12]=1>ClCCl>[ClH:10].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH2:23][C:22]2[NH:9][C:4]3[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][C:5]=3[N:8]=2)[CH2:18][C:19]([OH:21])=[O:20])=[C:13]([CH3:25])[CH:12]=1

Participants

4

Reactant 2

HCID 112070494-Iodobenzene-1,2-diamineHCID 86662457HCID 86662457, compound

Product 1

HCID 45381313HCID 45381313, compoundYield 125.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-iodo-1,2-phenylenediamine (0.47 g) in dichloromethane (2 ml) the solution of 3-(4-chloro-2-methylphenyl)glutaric anhydride (0.48 g) in dichloromethane (2 ml) was added with stirring at rt. Almost instantaneously an resinous precipitate is formed. After 1 h the mixture was cooled in an ice bath and the solvent was removed by decantation. The residue is dissolved in acetic acid (3 ml). Conc. HCl (1 ml) is added and the resulting solution is heated to reflux for 1 h. All volatiles are removed at the water aspirator and the residue is triturated with acetic acid and acetone to leave 3-(4-chloro-2-methylphenyl)-4-(5-iodo-2-benzimidazolyl)butanoic acid HCl (0.62 g) as light brown solid.

Workup

  1. customAlmost instantaneously an resinous precipitate is formed
  2. temperatureAfter 1 h the mixture was cooled in an ice bath
  3. customthe solvent was removed by decantation
  4. dissolutionThe residue is dissolved in acetic acid (3 ml)
  5. additionConc. HCl (1 ml) is added
  6. temperaturethe resulting solution is heated
  7. temperatureto reflux for 1 h
  8. customAll volatiles are removed at the water aspirator
  9. customthe residue is triturated with acetic acid and acetone

Sources & evidence

ORD record
ord-62cbf3f3b69446f38a5680439659c56c
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

Loading…