Oxalyl chloride → HCID 18680910, compound

HRID 276006Notes

Reaction equation

HRID 276006 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C(C1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[N:15]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:14]=2[CH:29]=1)(O)=O>C(Cl)Cl.CN(C)C=O>[ClH:4].[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][N:15]1[C:14]2[CH:29]=[C:1]([C:2]([Cl:4])=[O:3])[CH:11]=[CH:12][C:13]=2[N:17]=[C:16]1[CH:18]1[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 18681159HCID 18681159, compound

Product 1

HCID 18680910HCID 18680910, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 6228DimethylformamideSolvent

Procedure

Oxalyl chloride (0.208 ml) was added dropwise to a suspension prepared by adding 390 mg of 6-carboxy-1-(2-chlorobenzyl)-2-cyclopropylbenzimidazole to 10 ml of methylene chloride containing 1 drop of N,N-dimethylformamide at room temperature over a period of several minutes. The mixture was stirred at the same temperature for 2 hours, and was then concentrated under reduced pressure. Isopropyl ether was added to the residue, and the mixture was pulverized to give 450 mg of 1-(2-chlorobenzyl)-6-chlorocarbonyl-2-cyclopropylbenzimidazole hydrochloride (60) as a white powder. Since this product was unstable, it was used as a starting material in the subsequent step without being purified.

Workup

  1. customprepared
  2. concentrationwas then concentrated under reduced pressure
  3. additionIsopropyl ether was added to the residue

Sources & evidence

ORD record
ord-a2ba4306d8044ec5b620c73916a02a7d
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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