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

HRID 735989노트

반응식

HRID 735989 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-f4542c30f65644e2bf117ee59843149a
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592477B2

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