Potassium Carbonate → N-but-3-ynyl-1-(3,4-dichlorophenyl)methanesulfonamide

HRID 2181490

反応式

HRID 2181490 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:8]([NH2:12])[CH2:9][C:10]#[CH:11].[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][S:22](Cl)(=[O:24])=[O:23])[CH:17]=[CH:18][C:19]=1[Cl:20]>O.C1COCC1>[CH2:8]([NH:12][S:22]([CH2:21][C:16]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=1)(=[O:24])=[O:23])[CH2:9][C:10]#[CH:11]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2794622(3,4-Dichlorophenyl)methanesulfonyl chlorideHCID 12221022But-3-yn-1-amine hydrochloride

生成物 1

HCID 11243293N-but-3-ynyl-1-(3,4-dichlorophenyl)methanesulfonamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of potassium carbonate (40.2 g, 296 mmol) in water (50 mL) and THF (50 mL) at 15-20° C. was added but-3-ynylamine hydrogen chloride (10.4 g, 98.5 mmol). Then, (3,4-dichlorophenyl)methanesulfonyl chloride (5, 30.7 g, 118 mmol) was added in portions during of a period of 30 ml. The mixture was stirred for 4 h at rt. THF is evaporated. The mixture is extracted with EtOAc (2×200 mL). The combined organic extracts were dried over Na4SO4. The solvent is evaporated to give a white solid (20.5 g, 71%%). 1H NMR (CDCl3): δ7.53 (d, 1H, J=2.0 Hz), 7.47 (d, 1H, J=4.2 Hz), 7.27 (m, 1H), 4.52 (t, 1H, J=6.2 Hz), 4.22 (s, 2H), 3.17 (dd, 2H, J=6.2 Hz, 12.5 Hz), 2.41 (m, 2H), 2.07 (m, 1H)

後処理

  1. customTHF is evaporated
  2. extractionThe mixture is extracted with EtOAc (2×200 mL)
  3. dry with materialThe combined organic extracts were dried over Na4SO4
  4. customThe solvent is evaporated
  5. customto give a white solid (20.5 g, 71%%)

出典と根拠

ORDレコード
ord-dad69e0732744019a920098e8d88bf90
出典データセット
uspto-grants-2005_05
特許番号
US06891065B2

関連ノート

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