Oxalyl chloride → 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoyl chloride

HRID 746501Notes

Reaction equation

HRID 746501 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[N:7]1([C:12]2[N:16]([CH2:17][C:18]3[CH:26]=[CH:25]C(C(O)=O)=[CH:20][CH:19]=3)[C:15]3[CH:27]=[CH:28][CH:29]=[CH:30][C:14]=3[N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1>C(Cl)(Cl)Cl>[N:7]1([C:12]2[N:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:1]([C:2]([Cl:4])=[O:3])=[CH:25][CH:26]=3)[C:15]3[CH:27]=[CH:28][CH:29]=[CH:30][C:14]=3[N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 121445344-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoic acid

Product 1

HCID 121445354-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Oxalyl chloride (4 mL) was added to a suspension of 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoic acid (0.28 g, 0.872 mmol) in chloroform (50 mL). The mixture was heated at reflux for 1 hour and then concentrated under vacuum. The residue was diluted with toluene, concentrated under vacuum and then dried under vacuum at ambient temperature over the weekend to provide crude 4-[(2-pyrrolidinyl-1H-benzimidazol-1yl)methyl]benzoyl chloride.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated under vacuum
  4. additionThe residue was diluted with toluene
  5. concentrationconcentrated under vacuum
  6. customdried under vacuum at ambient temperature over the weekend

Sources & evidence

ORD record
ord-374c1d65b0224bc8ab63552b44f2d36b
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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