Dimethylformamide → HCID 13015380, compound

HRID 1863354Notes

Reaction equation

HRID 1863354 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][C:23]([OH:25])=[O:24])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[Li].CI.[CH3:29]N(C=O)C>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][C:23]([O:25][CH3:29])=[O:24])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 3028194LithiumHCID 13015379HCID 13015379, compound

Product 1

HCID 13015380HCID 13015380, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4,5-bis(p-methoxyphenyl)-2-thiazoleacetic acid, lithium salt (8.82 g.; 0.024 mole), methyl iodide (17.4 g.; 0.122 mole) and DMF (100 ml.) was stirred at ambient temperature for 16 hours. The mixture was poured into water (1.5 l.) and extracted with methylene chloride (500 ml.). The organic layer was washed with water (3×1.5 l.), saturated sodium bicarbonate (1.0 l.), water (1.5 l.), dried (sodium sulfate), and concentrated in vacuo. The oily residue was dissolved in acetone and applied directly to a Florisil-packed (340 ml.) gravity column (Florisil previously equilibrated with solvent mixture; 500 ml. packing: 100 ml. solvent). The sample was eluted with 5% acetone in hexane. The recovered product was recrystallized from diethyl ether-pentane to afford 3.32 g. (37% yield) of 4,5-bis(p-methoxyphenyl)-2-thiazoleacetic acid, methyl ester; m.p. 79°-81.5°.

Workup

  1. extractionextracted with methylene chloride (500 ml.)
  2. washThe organic layer was washed with water (3×1.5 l.), saturated sodium bicarbonate (1.0 l.), water (1.5 l.)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe oily residue was dissolved in acetone
  6. washThe sample was eluted with 5% acetone in hexane
  7. customThe recovered product was recrystallized from diethyl ether-pentane
  8. customto afford 3.32 g

Sources & evidence

ORD record
ord-abf6b1b44573437bb30aa4fcce7cf0ba
Source dataset
uspto-grants-1979_09
Patent number
US04168315

Reaction notes

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