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

HRID 735989Notes

Reaction equation

HRID 735989 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-f4542c30f65644e2bf117ee59843149a
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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