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

HRID 1699617

반응식

HRID 1699617 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′-carbonyldiimidazole (0.431 g) is added all at once to an N,N-dimethylformamide (15 ml) solution of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (0.400 g) (example 75), and the solution is stirred for one hour at room temperature. Subsequently, an N,N-dimethylformamide (5 ml) solution of 4-methoxybenzenesulfonamide (0.498 g) and diazabicycloundecene (0.405 g) is added, and the solution is stirred for 67 hours at 100° C. The reaction solution is cooled and the solvent is removed through evaporation under reduced pressure. Water and chloroform are added to the residue. While being stirred, 10% hydrochloric acid is added until the aqueous layer became acidic. The organic layer, which is obtained through chloroform extraction (twice), is washed with a saturated sodium bicarbonate aqueous solution, and the solvent is removed through evaporation under reduced pressure. After purification using silica gel column chromatography (eluate: chloroform/methanol=100/2˜100/10) and then concentration, crystals are formed in a mixture solution of ethyl acetatc and diethylether. The crystals are separated through filtration, dried, and thus, 1-(2-chlorobenzyl)-6-(4-methoxybenzenesulfonylcarbamoyl)-2-methylbenzimidazole (0.450 g) is obtained.

후처리

  1. stirringthe solution is stirred for 67 hours at 100° C
  2. temperatureThe reaction solution is cooled
  3. customthe solvent is removed through evaporation under reduced pressure
  4. additionWater and chloroform are added to the residue
  5. stirringWhile being stirred
  6. addition10% hydrochloric acid is added until the aqueous layer
  7. customThe organic layer, which is obtained through chloroform extraction (twice),
  8. washis washed with a saturated sodium bicarbonate aqueous solution
  9. customthe solvent is removed through evaporation under reduced pressure
  10. customAfter purification
  11. concentrationconcentration, crystals
  12. customare formed in a mixture solution of ethyl acetatc and diethylether
  13. customThe crystals are separated through filtration
  14. customdried

출처 및 근거

ORD 기록
ord-d94142da5d69439eb0d2042efd00b8a2
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348032B1

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