1,1'-Carbonyldiimidazole → 3-[3-(4-pyridylthio)propyl]quinazoline-2,4(1H,3H)-dione

HRID 6178

Reaction equation

HRID 6178 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:5].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>O1CCCC1>[N:14]1[CH:15]=[CH:16][C:11]([S:10][CH2:9][CH2:8][CH2:7][N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:1][C:21]2=[O:22])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 190790734-[3-(2-Aminobenzoylamino)propylthio]pyridine

Product 1

HCID 190790923-[3-(4-pyridylthio)propyl]quinazoline-2,4(1H,3H)-dioneYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, to a solution of 718 mg (2.5 mmol) of 4-[3-(2-aminobenzoylamino)propylthio]pyridine in 15 ml of tetrahydrofuran. 811 mg (5.0 mmol) of 1,1'carbonyldiimidazole was added, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was dissolved in chloroform. The solution was washed with water and dried. The solvent was distilled off and the residue was recrystallized from ethanol/chloroform/ether to give 514 mg of the desired product (65.7% yield, white crystals).

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customthe residue was recrystallized from ethanol/chloroform/ether

Sources & evidence

ORD record
ord-ec2bad3e6dba47c4a66e47e6b4dbd056
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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