Hydrochloric Acid → HCID 18315563, compound

HRID 276049Notes

Reaction equation

HRID 276049 reaction equation
[CH2:1]([C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:11]2[CH:22]=[C:23]([C:26](O)=[O:27])[CH:24]=[CH:25][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]1([S:35]([NH2:38])(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.Cl>CN(C)C=O>[C:29]1([S:35]([NH:38][C:26]([C:23]2[CH:24]=[CH:25][C:10]3[N:9]=[C:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[N:12]([CH2:13][C:14]4[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=4[Cl:21])[C:11]=3[CH:22]=2)=[O:27])(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 18315473HCID 18315473, compoundHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18315563HCID 18315563, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N′-carbonyldiimidazole (0.248 g) was added at a time to a solution of 0.315 g of 2-benzyl-6-carboxy-1-(2,4-dichlorobenzyl)benzimidazole in 5 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Subsequently, a solution of 0.240 g of benzenesulfonamide and 0.233 g of diazabicycloundecene in 4 ml of N,N-dimethylformamide was added thereto, and the mixture was stirred at 100° C. for 62 hours. The reaction solution was cooled, and the solvent was distilled off under reduced pressure. Water and chloroform were added to the residue, and 10% hydrochloric acid was added thereto while being mixed until the aqueous layer was acidified. The solution was extracted twice with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, and a part of the solvent was distilled off under reduced pressure. To the residue were added 4 ml of methanol and 4 ml of a 20% potassium hydrogencarbonate aqueous solution to form a uniform solution. This solution was then adjusted to a pH of from 5 to 6 with 10% hydrochloric acid. The crystals precipitated were separated through filtration, and were dried to give 0.310 g of 6-benzenesulfonylcarbamoyl-2-benzyl-1-(2,4-dichlorobenzyl)benzimidazole (244).

Workup

  1. stirringthe mixture was stirred at 100° C. for 62 hours
  2. temperatureThe reaction solution was cooled
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater and chloroform were added to the residue, and 10% hydrochloric acid
  5. additionwas added
  6. additionwhile being mixed until the aqueous layer
  7. extractionThe solution was extracted twice with chloroform
  8. washThe resulting organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  9. distillationa part of the solvent was distilled off under reduced pressure
  10. additionTo the residue were added 4 ml of methanol and 4 ml of a 20% potassium hydrogencarbonate aqueous solution
  11. customto form a uniform solution
  12. customThe crystals precipitated
  13. customwere separated through filtration
  14. customwere dried

Sources & evidence

ORD record
ord-07e2baf9851b4b05b7c69baee13c2afb
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

Loading…