1-Bromotridecan-2-one → 4-(4-Undecyl-1,3-thiazol-2-yl)benzaldehyde

HRID 735989ノート

反応式

HRID 735989 の反応式
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[O:16]1CCO[CH:17]1[C:21]1[CH:26]=[CH:25][C:24]([C:27](=[S:29])[NH2:28])=[CH:23][CH:22]=1>CCO>[CH2:4]([C:3]1[N:28]=[C:27]([C:24]2[CH:25]=[CH:26][C:21]([CH:17]=[O:16])=[CH:22][CH:23]=2)[S:29][CH:2]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

4

反応物 2

HCID 2371331-Bromotridecan-2-oneHCID 27787314-(1,3-Dioxolan-2-yl)benzene-1-carbothioamide

生成物 1

HCID 865985394-(4-Undecyl-1,3-thiazol-2-yl)benzaldehyde収率 59%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 1-bromotridecan-2-one (5.54 g, 20 mmol) and 4-(1,3-dioxolan-2-yl)benzenecarbothioamide (4.19 g, 20 mmol) in EtOH (50 mL) was refluxed overnight. After evaporation of the solvent, the residue was taken up in ether, washed with water, brine, dried over MgSO4, filtered. The solvents were evaporated under vacuum to give a yellow oil. Purification on silicagel gave the title product as a yellow solid (4.05 g, 59%). 1H NMR (CDCl3, 300 MHz) δ 10.0 (s, 1H), 8.11 (d, 2H, J=8.3 Hz), 7.93 (d, 2H, J=8.6 Hz), 6.98 (s, 1H), 2.84 (t, 2H, J=7.2 Hz), 1.78-1.72 (m, 2H), 1.50-1.20 (m, 16H), 0.87 (t, 3H, J=6.8 Hz). M+(LC/MS(ESI)): 344.3

後処理

  1. customAfter evaporation of the solvent
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvents were evaporated under vacuum
  6. customto give a yellow oil
  7. customPurification on silicagel

出典と根拠

ORDレコード
ord-f4542c30f65644e2bf117ee59843149a
出典データセット
uspto-grants-2009_09
特許番号
US07592477B2

反応ノート

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