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

HRID 2210186Notes

Reaction equation

HRID 2210186 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-4bceee421e33488e82c6d41b7f2531c5
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

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