Dichloromethane → HCID 45381311, compound

HRID 1402813Notes

Reaction equation

HRID 1402813 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]1[CH2:23][C:22](=O)[O:21][C:19](=[O:20])[CH2:18]1.[Cl:25]CCl>>[I:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:22]([CH2:23][CH:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH3:10])[CH2:18][C:19]([OH:21])=[O:20])[NH:9][C:4]=2[CH:3]=1.[ClH:25]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 112070494-Iodobenzene-1,2-diamineHCID 82126207HCID 82126207, compound

Product 1

HCID 45381311HCID 45381311, compound

Procedure

To a solution of 4-iodo-1,2-phenylenediamine (0.47 g) in dichloromethane (3 ml) the solution of 3-(2-methylphenyl)glutaric anhydride (0.41 g) in dichloromethane (4 ml) was added with stirring at rt. Almost instantaneously an resinous precipitate is formed. After 1 h at rt all volatiles are removed in vacuo and the residue is taken up in 1,4-dioxane (2 ml). 4M HCl in 1,4-dioxane (3 ml) is added and the resulting dark solution is heated to reflux for 1 h. Again all volatiles are removed at the water aspirator and the residue is recrystallised from EtOAc/methanol to give 4-(5-iodo-2-benzimidazolyl)-3-(2-methylphenyl)butanoic acid•HCl (0.49 g) as light brown solid.

Workup

  1. customAlmost instantaneously an resinous precipitate is formed
  2. customAfter 1 h at rt all volatiles are removed in vacuo
  3. addition4M HCl in 1,4-dioxane (3 ml) is added
  4. temperaturethe resulting dark solution is heated
  5. temperatureto reflux for 1 h
  6. customAgain all volatiles are removed at the water aspirator
  7. customthe residue is recrystallised from EtOAc/methanol

Sources & evidence

ORD record
ord-7433b539ad5d4127aa5535af4094455a
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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