Dimethylformamide → N-(4-(5-Cyano-1-ethyl-1H-pyrrol-2-yl)phenyl)ethanesulfonamide

HRID 1591839노트

반응식

HRID 1591839 반응식
[C:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[CH3:20][C:21](C)([O-])C.[K+].C(I)C.CN(C)C=O>O1CCCC1>[C:1]([C:3]1[N:7]([CH2:20][CH3:21])[C:6]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 16051191N-[4-(5-Cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 16051192N-(4-(5-Cyano-1-ethyl-1H-pyrrol-2-yl)phenyl)ethanesulfonamide수율 11%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-[4-(5-cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamide (0.160 g, 0.58 mmol) was dissolved in tetrahydrofuran (10 mL). Potassium tert-butoxide (1.25 mL of a 1 M solution, 1.25 mmol) was dropwise added and the mixture stirred 15 minutes. Ethyl iodide (0.046 mL, 0.58 mmol) was dropwise added, followed by dimethyl formamide (5 mL) and the mixture stirred for 4 hours. The mixture was then partitioned between saturated ammonium chloride and ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated. The residue was purified by silica gel Flash Chromatography (hexane/ethyl acetate; 7:3) to afford the title compound (0.020 g, 11%).

후처리

  1. stirringthe mixture stirred for 4 hours
  2. customThe mixture was then partitioned between saturated ammonium chloride and ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel Flash Chromatography (hexane/ethyl acetate; 7:3)

출처 및 근거

ORD 기록
ord-d52bfe79270f4b6bbb96a594325b8dc6
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291643B2

반응 노트

불러오는 중…