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

HRID 1591839ノート

反応式

HRID 1591839 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-d52bfe79270f4b6bbb96a594325b8dc6
出典データセット
uspto-grants-2007_11
特許番号
US07291643B2

反応ノート

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