Oxalyl chloride → Carbonyl benzimidazole

HRID 1072539Notes

Reaction equation

HRID 1072539 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.COC1CCC(C(O)=O)CC1.NC1C=CC(C2[NH:26][C:27]3[CH:33]=[CH:32][C:31](N)=[CH:30][C:28]=3[N:29]=2)=CC=1>C(Cl)Cl.CN(C=O)C.N1C=CC=CC=1>[C:1](=[C:2]1[N:29]=[C:28]2[CH:30]=[CH:31][CH:32]=[CH:33][C:27]2=[N:26]1)=[O:5]

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 736153Rac-(1r,4r)-4-methoxycyclohexane-1-carboxylic acidHCID 178507432HCID 178507432, compound

Product 1

HCID 22387228Carbonyl benzimidazole

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Bis-4-methoxyclohexyl carbonyl benzimidazole was synthesized as follows: Oxalyl chloride, (1.07. ml, 2 M in CH2Cl2) was added to 4-methoxy-cyclohexane carboxylic acid (0.338 g, 2.14 mmole) followed by one drop DMF. The mixture was allowed to react at RT for 1.0 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.

Workup

  1. customto react at RT for 1.0 hour
  2. temperatureThe reaction was cooled
  3. filtrationthe precipitate filtered
  4. washwashed with NaHCO3 and hexanes

Sources & evidence

ORD record
ord-cfd0421849c2497a88f7d19f0c404465
Source dataset
uspto-grants-2005_06
Patent number
US06911462B2

Reaction notes

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