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2-Bromo-1,2-bis(4-methoxyphenyl)ethanone → Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)-

HRID 542861
Notes
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Reaction equation

HRID 542861 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[S:8])[NH2:7].Br[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>C(#N)C>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:10]2[N:7]=[C:6]([C:2]3[NH:1][CH:5]=[CH:4][CH:3]=3)[S:8][C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[CH:26][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3441532-Bromo-1,2-bis(4-methoxyphenyl)ethanoneHCID 135893131H-Pyrrole-2-carbothioamide

Product 1

HCID 3063502Thiazole, 4,5-bis(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)-Yield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Pyrrole-2-carbothioamide (cf. J. Org. Chem., 38, 667, 1973) (1.51 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). The mixture is stirred at 60° C. for 50 minutes. After the reaction, the reaction mixture is distilled under reduced pressure to remove the solvent. To the resulting residue are added chloroform and aqueous solution of 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 ligroin to give 4,5-bis(4-methoxyphenyl)-2-(pyrrol-2-yl)-thiazole (3.74 g, yield: 86%).

Workup

  1. customAfter the reaction
  2. distillationthe reaction mixture is distilled under reduced pressure
  3. customto remove the solvent
  4. additionTo the resulting residue are added chloroform and aqueous solution of 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 ligroin

Sources & evidence

ORD record
ord-fd05419ddc56478ea505e8e752768523
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04659726

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes