Sodium Iodide → 2-(3,4-Diethoxyphenyl)-4-(2-acetyl-1-pyrrolyl)methylthiazole

HRID 1421983Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([CH2:18]Cl)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[C:20]([C:23]1[NH:24][CH:25]=[CH:26][CH:27]=1)(=[O:22])[CH3:21].[I-].[Na+].[OH-].[Na+]>O.CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([CH2:18][N:24]3[CH:25]=[CH:26][CH:27]=[C:23]3[C:20](=[O:22])[CH3:21])[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

In a mixed solvent consisting of 2 ml of dimethylformamide and 0.2 ml of water were dissolved 200 mg of 2-(3,4-diethoxyphenyl)-4-chloromethylthiazole, 73 mg of 2-acetylpyrrole, 200 mg of sodium iodide and 200 mg of sodium hydroxide. The solution was stirred at 80° C. for 4 hours. The reaction mixture was subjected to distillation to remove the solvent. To the residue were added 30 ml of dichloromethane and 20 ml of water, and phase separation was conducted. The organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was recrystallized from methanol to obtain 60 mg of 2-(3,4-diethoxyphenyl)-4-(2-acetyl-1-pyrrolyl)methylthiazole as white acicular crystals.

Workup

distillationThe reaction mixture was subjected to distillation
customto remove the solvent
additionTo the residue were added
custom30 ml of dichloromethane and 20 ml of water, and phase separation
washThe organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution
customdried
distillationsubjected to distillation
customto remove the solvent
customThe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-23cca9b6ec8e48369c7c9e1a023d75b3
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080764

Reaction notes

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