Cesium carbonate → 3-[3-(4-Phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

HRID 2251734노트

반응식

HRID 2251734 반응식
[OH:1][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Br[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][C:18]=1[CH2:30][CH2:31][CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[O:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][CH2:13][O:1][C:2]2[CH:3]=[C:4]([S:8]([NH2:11])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[C:18]([CH2:30][CH2:31][CH3:32])[CH:19]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 6375573-HydroxybenzenesulfonamideHCID 187722731-(3-bromopropoxy)-4-phenoxy-2-propylBenzene

생성물 1

HCID 586471293-[3-(4-Phenoxy-2-propylphenoxy)propoxy]benzenesulfonamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-hydroxybenzenesulfonamide (0.5 g, 2.89 mmol) and 1-(3-bromopropoxy)-4-phenoxy-2-propylbenzene (1.01 g, 2.89 mmol) with cesium carbonate (1.04 g, 3.18 mmol) in dry DMF (10 mL) was stirred at 50° C. for 5 h. The reaction suspension was cooled to room temperature and concentrated under vacuum to an orange residue. The residue was partitioned between ethyl acetate and water. The ethyl acetate phase was dried over sodium sulfate, filtered, and concentrated to an oil. The oil was chromatographed over silica gel with hexanes/ethyl acetate (2:1) to provide the title compound.

후처리

  1. concentrationconcentrated under vacuum to an orange residue
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThe oil was chromatographed over silica gel with hexanes/ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-069dc8b73caf44fab2da1d4dfbf381bf
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319170B2

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