5-Methyl-2-thiophenecarboxaldehyde → HCID 20098193, compound

HRID 1768907Notes

Reaction equation

HRID 1768907 reaction equation
[CH:1]([C:4]1([CH3:17])[C:8](=[O:9])[NH:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)=[N:5]1)([CH3:3])[CH3:2].C[Li].[CH3:20][C:21]1[S:25][C:24]([CH:26]=[O:27])=[CH:23][CH:22]=1>O1CCCC1.C(OCC)C.C(Cl)Cl>[OH:27][CH:26]([C:15]1[C:10]([C:6]2[NH:7][C:8](=[O:9])[C:4]([CH:1]([CH3:3])[CH3:2])([CH3:17])[N:5]=2)=[N:11][CH:12]=[C:13]([CH3:16])[CH:14]=1)[C:24]1[S:25][C:21]([CH3:20])=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 13730891HCID 13730891, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20098193HCID 20098193, compoundYield 13%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-isopropyl-4-methyl-2-(5-methyl-2-pyridyl)-2-imidazolin-5-one (10.0 g, 0.043 mol) in anhydrous tetrahydrofuran (200 mL) is cooled to -78° C. and treated with a 1.5 molar solution of methyl lithium in diethyl ether (60.6 mL). The resultant suspension is stirred at -78° C. for 30 minutes and at 0° C. for 30 minutes. The reaction mixture is recooled to -78° C. and 5-methyl-2-thiophenecarboxaldehyde (15.35 g, 0.043 mol) is added dropwise. After 30 minutes, the cooling bath is removed and the reaction mixture is stirred at room temperature overnight then diluted with water. The aqueous mixture is acidified to pH 6 with acetic acid and extracted with diethyl ether. The combined organic extracts are washed with water, dried (Na2SO4) and concentrated in vacuo to obtain an orange oil. Chromatography of the oil using silica gel and a 20% diethyl ether in methylene chloride mixture gives a yellow oil which is triturated with diethyl ether to obtain the title product as a white solid (2.0 g, mp 147°-148° C.).

Workup

  1. customis recooled to -78° C.
  2. customthe cooling bath is removed
  3. additionthen diluted with water
  4. extractionextracted with diethyl ether
  5. washThe combined organic extracts are washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto obtain an orange oil
  9. customis triturated with diethyl ether

Sources & evidence

ORD record
ord-6948a2e5f06d4842b5dac6659073a806
Source dataset
uspto-grants-1995_01
Patent number
US05380698

Reaction notes

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