9-Acetyl-9H-carbazole → HCID 66850646, 화합물

HRID 873666

반응식

HRID 873666 반응식
[CH:1]1[C:13]2[N:12]([C:14](=[O:16])[CH3:15])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][C:19]=1[S:27](=[O:30])(=[O:29])[NH2:28].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:14]([N:12]1[C:11]2[CH:10]=[C:9]([C:22]([C:21]3[CH:25]=[CH:26][C:18]([Cl:17])=[C:19]([S:27]([NH2:28])(=[O:29])=[O:30])[CH:20]=3)=[O:23])[CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)(=[O:16])[CH3:15]

참가 물질

5

반응물 3

HCID 958379-Acetyl-9H-carbazoleHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 66850646HCID 66850646, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

To a solution of 1 g of 1-carbazol-9-yl-ethanone and 2.43 g of 4-chloro-3-sulfamoyl-benzoyl chloride in methylene chloride (20 mL) is added 2.55 g of aluminum chloride. The mixture is stirred at 50° C. overnight. The solution is then cooled at −78° C., quenched with a 6 N HCl solution and allowed to warm up to room temperature. Methylene chloride is added to dissolve the precipitate and the solution is extracted, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is loaded on Celite and purified by silica gel chromatography (1:1 hexanes/ethyl acetate) to afford 5-(9-acetyl-9H-carbazole-2-carbonyl)-2-chloro-benzenesulfonamide as yellow foam. MS (m/z): 427 (M+1). HPLC Reverse Phase (Nucleosil 100-5 C18, gradient 10→100% CH3CN in 5 min) room temperature=5.35 minutes.

후처리

  1. temperatureThe solution is then cooled at −78° C.
  2. customquenched with a 6 N HCl solution
  3. temperatureto warm up to room temperature
  4. additionMethylene chloride is added
  5. dissolutionto dissolve the precipitate
  6. extractionthe solution is extracted
  7. washwashed with a saturated sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by silica gel chromatography (1:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-b058d22797e14c7aaa7d8336d8ca5540
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975439B2

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