1,1'-Carbonyldiimidazole → 3-(2,4-Dichlorobenzyl)-2-methyl-5-(1-n-pentanesulfonylcarbamoyl)benzo[b]thiophene

HRID 1699954노트

반응식

HRID 1699954 반응식
[C:1]([C:4]1[CH:22]=[CH:21][C:7]2[S:8][C:9]([CH3:20])=[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[C:6]=2[CH:5]=1)([OH:3])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:35]([S:40]([NH2:43])(=[O:42])=[O:41])[CH2:36][CH2:37][CH2:38][CH3:39].C1CCN2C(=NCCC2)CC1>CN(C)C=O>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[CH2:11][C:10]1[C:6]2[CH:5]=[C:4]([C:1](=[O:3])[NH:43][S:40]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=[O:42])=[O:41])[CH:22]=[CH:21][C:7]=2[S:8][C:9]=1[CH3:20]

참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109206961-PentanesulfonamideHCID 223878405-Carboxy-3-(2,4-dichlorobenzyl)-2-methylbenzo[b]thiophene

생성물 1

HCID 223877973-(2,4-Dichlorobenzyl)-2-methyl-5-(1-n-pentanesulfonylcarbamoyl)benzo[b]thiophene수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In the same manner as in Example 1, 5-carboxy-3-(2,4-dichlorobenzyl)-2-methylbenzo[b]thiophene (440 mg, 1.25 mmol) was suspended in dimethylformamide and carbonyldiimidazole (305 mg, 1.88 mmol) was added, which was followed by stirring at room temperature for 1 hr. Then, 1-n-pentanesulfonamide (284 mg, 1.88 mmol) and DBU (286 mg, 1.88 mmol) were added and the mixture was refluxed under heating at 100° C. for 15 hr. The reaction mixture was concentrated under reduced pressure and water and 3N hydrochloric acid were added to acidify the mixture. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The residual oil was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/2) and recrystallized from 2-propanol-n-hexane to give 3-(2,4-dichlorobenzyl)-2-methyl-5-(1-n-pentanesulfonylcarbamoyl)benzo[b]thiophene (410 mg, 68%) as colorless crystals.

후처리

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating at 100° C. for 15 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure and water and 3N hydrochloric acid
  4. additionwere added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residual oil was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/2)
  11. customrecrystallized from 2-propanol-n-hexane

출처 및 근거

ORD 기록
ord-5d600b81295c446d8337c41c8eb9b9c3
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348474B1

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