2-Bromo-1,2-bis(4-methoxyphenyl)ethanone → 4,5-Bis(4-methoxyphenyl)-2-(1-ethylpyrrol-2-yl)thiazole

HRID 542863Notes

Reaction equation

HRID 542863 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8](=[S:10])[NH2:9])[CH3:2].Br[CH:12]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>C(#N)C>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:12]2[N:9]=[C:8]([C:4]3[N:3]([CH2:1][CH3:2])[CH:7]=[CH:6][CH:5]=3)[S:10][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 3441532-Bromo-1,2-bis(4-methoxyphenyl)ethanoneHCID 30634971-Ethyl-1H-pyrrole-2-carbothioamide

Product 1

HCID 135893124,5-Bis(4-methoxyphenyl)-2-(1-ethylpyrrol-2-yl)thiazoleYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

1-Ethylpyrrole-2-carbothioamide obtained in Reference Example 1 (1.85 g, 12 mmole) and α-bromo-4,4'-dimethoxydeoxybenzoin (cf. Aust. J. Chem., 8, 385, 1955) (4.02 g, 12 mmole) are dissolved in acetonitrile (120 ml), and the mixture is stirred at 60° C. for 50 minutes. After the reaction, the mixture is distilled under reduced pressure to remove the solvent. To the residue are added chloroform and aqueous sodium carbonate, and the mixture is shaken. The chloroform layer is taken, and the aqueous layer is further extracted with chloroform. The chloroform layers are combined, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue is recrystallized from n-hexane to give 4,5-bis(4-methoxyphenyl)-2-(1-ethylpyrrol-2-yl)thiazole (3.6 g, yield: 77%).

Workup

  1. customAfter the reaction
  2. distillationthe mixture is distilled under reduced pressure
  3. customto remove the solvent
  4. additionTo the residue are added chloroform and aqueous sodium carbonate
  5. stirringthe mixture is shaken
  6. extractionthe aqueous layer is further extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue is recrystallized from n-hexane

Sources & evidence

ORD record
ord-a22f2977ee104f9d8a565848dabab7fd
Source dataset
uspto-grants-1987_04
Patent number
US04659726

Reaction notes

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