Dimethyl Sulfoxide → 7-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanal

HRID 1616536Notes

Reaction equation

HRID 1616536 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[S:22][CH:23]=2)=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[O:31])[S:22][CH:23]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 684914117-[4-(4-Methoxyphenyl)thiazol-2-yl]heptan-1-ol

Product 1

HCID 593240777-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanalYield 99.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Add anhydrous dimethyl sulfoxide (0.25 mL, 3.52 mmol) dropwise over 2 minutes to a solution of oxalyl chloride (393 mg, 3.10 mmol) in methylene chloride (10 mL) at −78° C. under nitrogen and stir the mixture for 20 minutes. Add a solution of 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptan-1-ol (0.609 g, 1.99 mmol) in methylene chloride (10 mL) dropwise in 5 minutes and then stir the mixture for 30 minutes. To this mixture, add triethylamine (1.0 mL, 7.2 mmol), stir and warm the reaction mixture to room temperature for 40 minutes. Dilute the mixture with ethyl acetate (100 mL), wash with brine (3×30 mL), dry over sodium sulfate and remove the solvent under reduced pressure to provide 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptanal (0.6 g, 99%): APCI mass spectrum m/z 304 [C17H21NO2S+H]+.

Workup

  1. stirringstir the mixture for 30 minutes
  2. stirringstir
  3. washwash with brine (3×30 mL)
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-722a218189f64f02be7d4b8e90c8a7c3
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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