Oxalyl chloride → Bis-(2,2,3,3-tetramethylcyclopropane) carbonyl benzimidazole

HRID 1072537Notes

Reaction equation

HRID 1072537 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH:9]1C(O)=O.NC1C=CC(C2[NH:25][C:26]3[CH:32]=[CH:31][C:30](N)=[CH:29][C:27]=3[N:28]=2)=CC=1>CN(C=O)C.N1C=CC=CC=1>[C:1](=[C:2]1[N:28]=[C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]2=[N:25]1)=[O:5].[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH2:9]1.[CH3:7][C:8]1([CH3:16])[C:10]([CH3:12])([CH3:11])[CH2:9]1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acidHCID 178507432HCID 178507432, compound

Product 1

HCID 86588257Bis-(2,2,3,3-tetramethylcyclopropane) carbonyl benzimidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Bis-(2,2,3,3-tetramethylcyclopropane) carbonyl benzimidazole was synthesized as follows: oxalyl chloride (1.07 ml, 2 M in CH2Cl2) was added to 2,2,3,3-tetramethylcyclopropane carboxylic acid (0.305 g, 2.14 mmole) followed by one drop DMF. The mixture was allowed to react at RT for 1 hour. To the above solution was added 2-(4-aminophenyl)-6-amino benzimidazole (0.200 g, 0.89 mmole) in pyridine (2 ml). The reaction was heated to 60° C. overnight. The reaction was cooled and the precipitate filtered and washed with NaHCO3 and hexanes. The resulting solid was purified by preparative HPLC to yield a solid that was >99% pure.

Workup

  1. customto react at RT for 1 hour
  2. temperatureThe reaction was cooled
  3. filtrationthe precipitate filtered
  4. washwashed with NaHCO3 and hexanes
  5. customThe resulting solid was purified by preparative HPLC
  6. customto yield a solid

Sources & evidence

ORD record
ord-41194472ce8e49ba9678d886bd8bcb0d
Source dataset
uspto-grants-2005_06
Patent number
US06911462B2

Reaction notes

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