4-Methoxybenzenesulfonamide → 1-(2-Chlorobenzyl)-6-(4-methoxybenzenesulfonylcarbamoyl)-2-methylbenzimidazole

HRID 276046

반응식

HRID 276046 반응식
[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)([OH:3])=O.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[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:3])[NH:33][S:30]([C:27]3[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:29][CH:28]=3)(=[O:31])=[O:32])[CH:5]=[CH:6][C:7]=2[N:11]=[C:10]1[CH3:12]

참가 물질

5

반응물 3

HCID 707894-MethoxybenzenesulfonamideHCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-MethylbenzimidazoleHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

생성물 1

HCID 183154771-(2-Chlorobenzyl)-6-(4-methoxybenzenesulfonylcarbamoyl)-2-methylbenzimidazole수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

N,N′-carbodiimidazole (0.431 g) was added at a time to a solution of 0.400 g of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole in 15 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Subsequently, a solution of 0.498 g of 4-methoxybenzenesulfonamide and 0.405 g of diazabicycloundecene in 5 ml of N,N-dimethylformamide was added thereto, and the mixed solution was stirred at 100° C. for 67 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 cooled until the aqueous layer was acidified. The resulting mixture was extracted twice with chloroform. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, and the solvent was distilled off under reduced pressure. The residue was purified through silica-gel column chromatography (eluent: a mixture of chloroform and methanol at a ratio of 100:2 to 100:10). The resulting product was concentrated, and was crystallized from a mixed solution of ethyl acetate and diethyl ether. The crystals were separated through filtration, and were dried to give 0.450 g of 1-(2-chlorobenzyl)-6-(4-methoxybenzenesulfonylcarbamoyl)-2-methylbenzimidazole (217).

후처리

  1. stirringthe mixed solution was stirred at 100° C. for 67 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. temperaturewhile being cooled until the aqueous layer
  7. extractionThe resulting mixture was extracted twice with chloroform
  8. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified through silica-gel column chromatography (eluent
  11. additiona mixture of chloroform and methanol at a ratio of 100:2 to 100:10)
  12. concentrationThe resulting product was concentrated
  13. customwas crystallized from a mixed solution of ethyl acetate and diethyl ether
  14. customThe crystals were separated through filtration
  15. customwere dried

출처 및 근거

ORD 기록
ord-d9d74093da1f4f27836be1da0c528f52
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352985B1

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