2-Bromo-1,2-bis(4-methoxyphenyl)ethanone → HCID 12637268, compound

HRID 1863353Notes

Reaction equation

HRID 1863353 reaction equation
[CH:1]([NH2:3])=[S:2].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH:13](Br)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1>C(#N)C>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]2[N:3]=[CH:1][S:2][C:12]=2[C:9]2[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[CH:11][CH:10]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 3441532-Bromo-1,2-bis(4-methoxyphenyl)ethanoneHCID 3005587Methanethioamide

Product 1

HCID 12637268HCID 12637268, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

An ethereal solution of thioformamide (0.153 mole) was concentrated in vacuo at less than 25°. The residue was slurried with acetonitrile (10 ml.) and cooled in an ice water bath. p-Methoxy-2-bromo-2-(p-methoxyphenyl)acetophenone (4.27 g.; 0.0128 mole) was dissolved in acetonitrile (50 ml.) and added via syringe to the above slurry. After stirring for 15 minutes in ice, the flask was refrigerated at 5°-10° for 16 hours. The solution was then stirred at ambient temperature for 70 hours before work up. The solvent was removed in vacuo and the residue was partitioned with ether and saturated sodium bicarbonate solution. The ether layer was washed with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dried (sodium sulfate), and concentrated in vacuo. The residue was chromatographed on silica gel 60 at low pressure with 5% ethyl acetate in benzene. Recrystallization from hexane:benzene (11:1) afforded 2.25 g. (59% yield) of 4,5-bis(p-methoxyphenyl)thiazole.

Workup

  1. temperaturecooled in an ice water bath
  2. additionadded via syringe to the above slurry
  3. waitthe flask was refrigerated at 5°-10° for 16 hours
  4. stirringThe solution was then stirred at ambient temperature for 70 hours before work up
  5. customThe solvent was removed in vacuo
  6. customthe residue was partitioned with ether and saturated sodium bicarbonate solution
  7. washThe ether layer was washed with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed on silica gel 60 at low pressure with 5% ethyl acetate in benzene
  11. customRecrystallization from hexane:benzene (11:1)
  12. customafforded 2.25 g

Sources & evidence

ORD record
ord-9085ebae26cc45c5bc99104471f229e3
Source dataset
uspto-grants-1979_09
Patent number
US04168315

Reaction notes

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