Benzenesulfonyl chloride → N-(2-(3-Chlorophenyl)pent-4-enyl)-N-methylbenzenesulfonamide

HRID 1737446ノート

反応式

HRID 1737446 の反応式
[CH3:1][NH:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)[CH2:5][CH:6]=[CH2:7].C(=O)(O)[O-].[Na+].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.O>[Cl:14][C:10]1[CH:9]=[C:8]([CH:4]([CH2:5][CH:6]=[CH2:7])[CH2:3][N:2]([CH3:1])[S:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:28])=[O:27])[CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 23285277N-Methyl-(2-(3-chlorophenyl)pent-4-enyl)amine

生成物 1

HCID 23285190N-(2-(3-Chlorophenyl)pent-4-enyl)-N-methylbenzenesulfonamide収率 61.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-Methyl-(2-(3-chlorophenyl)pent-4-enyl)amine (202 mg, 1.03 mmol) was dissolved in 10 mL of ethyl acetate. A solution of sodium bicarbonate (766 mg, 10.3 mmol) in water (10 mL) was added followed by benzenesulfonyl chloride (363 mg, 4.06 mmol), and the heterogeneous mixture was stirred overnight at room temperature. The mixture was extracted with 5 mL of ethyl acetate followed by an additional 2×15 mL of ethyl acetate. The combined organic layers were dried over sodium sulfate, decanted, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with 10-20% ethyl ether in hexane to give 223 mg the title compound. 1NMR (400 MHz, CDCl3): δ 7.72 (d, 2H, J=8 Hz), 7.58 (tt, 1H, J=8, 1 Hz), 7.50 (t, 2H, J=8 Hz), 7.24 (d, 1H, J=8 Hz), 7.20 (dt, 1H, J=8, 1 Hz), 7.14 (t, 1H, J=1 Hz), 7.10 (dt, 1H, J=8, 1 Hz), 5.63 (ddt, 1H, J=17, 10, 7 Hz), 5.00 (dm, 1H, J=17 Hz),4.97 (dm, 1H, J=10 Hz) 3.42-3.34 (m, 1H), 3.00-2.90 (m, 2H), 2.61 (s, 3H), 2.56 (dtm, 1H, J=14, 6 Hz), 2.36 (dtm, 1H, J=14, 7 Hz). Mass spectrum (NH3 /CI): m/z=350 (M+1).

後処理

  1. extractionThe mixture was extracted with 5 mL of ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customdecanted
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with 10-20% ethyl ether in hexane

出典と根拠

ORDレコード
ord-1cd633090612478788375293786312df
出典データセット
uspto-grants-1999_10
特許番号
US05962462

反応ノート

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