Dichloromethane → HCID 178423945, compound

HRID 1402938Notes

Reaction equation

HRID 1402938 reaction equation
[CH3:1][C:2]1[C:3]([NH2:9])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[CH:20]1[CH2:26][C:25](=O)[O:24][C:22](=[O:23])[CH2:21]1.[Cl:28]CCl>>[ClH:28].[CH3:1][C:2]1[C:3]2[NH:9][C:25]([CH2:26][CH:20]([C:11]3[CH:12]=[CH:13][C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:10]=3)[CH2:21][C:22]([OH:24])=[O:23])=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 175932,3-DiaminotolueneHCID 86662458HCID 86662458, compound

Product 1

HCID 178423945HCID 178423945, compound

Procedure

3-Methyl-1,2-phenylenediamine (61 mg) and 3-(2-naphthyl)glutaric anhydride (120 mg) were dissolved in dichloromethane (2 ml) with heating. The solution was stirred at rt for 1 h. The solvent was removed and the residue was dissolved in 1,4-dioxane (1 ml) with heating. 4M HCl in 1,4-dioxane (1 ml) was added and the solution was heated to reflux for 1 h. The precipitate formed was isolated by suction filtration, washed with 1,4-dioxane, and dried to give 4-(4-methyl-2-benzimidazolyl)-3-(2-naphthyl)butanoic acid HCl (162 mg) as beige coloured solid.

Workup

  1. temperaturewith heating
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in 1,4-dioxane (1 ml)
  4. temperaturewith heating
  5. addition4M HCl in 1,4-dioxane (1 ml) was added
  6. temperaturethe solution was heated
  7. temperatureto reflux for 1 h
  8. customThe precipitate formed
  9. customwas isolated by suction filtration
  10. washwashed with 1,4-dioxane
  11. customdried

Sources & evidence

ORD record
ord-4c22dc2907064cb9bcb29afeb8676a4d
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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