Trifluoromethylsulfonamide → HCID 18315509, compound

HRID 276045Notes

Reaction equation

HRID 276045 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:8]=2[CH:21]=1)(O)=[O:2].[F:22][C:23]([F:29])([F:28])[S:24]([NH2:27])(=[O:26])=[O:25].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[ClH:20].[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:9]1[C:8]2[CH:21]=[C:4]([C:1](=[O:2])[NH:27][S:24]([C:23]([F:29])([F:28])[F:22])(=[O:26])=[O:25])[CH:5]=[CH:6][C:7]=2[N:11]=[C:10]1[CH3:12]

Participants

5

Reactant 3

HCID 79001TrifluoromethylsulfonamideHCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-MethylbenzimidazoleHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18315509HCID 18315509, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N′-carbonyldiimidazole (0.647 g) was added at a time to a solution of 0.600 g of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole in 20 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Subsequently, a solution of 0.596 g of trifluoromethanesulfonamide and 0.609 g of diazabicycloundecene in 5 ml of N,N-dimethylformamide was added thereto, and the mixture was stirred at 100° C. for 72 hours. The reaction solution was cooled, and the solvent was distilled off under reduced pressure. Water and ethyl acetate were added to the residue, and 10% hydrochloric acid was added thereto while being stirred until the aqueous layer was acidified. The crystals precipitated were washed with a mixed solvent of 25 ml of ethanol and 25 ml of methanol. The crystals were dried to give 0.420 g of 1-(2-chlorobenzyl)-2-methyl-6-trifluoromethanesulfonylcarbamoylbenzimidazole hydrochloride (214).

Workup

  1. stirringthe mixture was stirred at 100° C. for 72 hours
  2. temperatureThe reaction solution was cooled
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater and ethyl acetate were added to the residue, and 10% hydrochloric acid
  5. additionwas added
  6. stirringwhile being stirred until the aqueous layer
  7. customThe crystals precipitated
  8. washwere washed with a mixed solvent of 25 ml of ethanol and 25 ml of methanol
  9. customThe crystals were dried

Sources & evidence

ORD record
ord-0712cbee9a5f46ffbaf4cc5e56848294
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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