1,1'-Thiocarbonyldiimidazole → 3-[3-(4-pyridylthio)propyl)quinazoline-2(1H)-thion-4(3H)-one

HRID 6179

Reaction equation

HRID 6179 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)=[S: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=[S:22])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 190790734-[3-(2-Aminobenzoylamino)propylthio]pyridine

Product 1

HCID 1317181783-[3-(4-pyridylthio)propyl)quinazoline-2(1H)-thion-4(3H)-oneYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, to a solution of 1.48 g (5.15 mmol) of 4-[3-(2-aminobenzoylamino)propylthio]pyridine in 30 ml of tetrahydrofuran, 1.84 g (10.3 mmol) of 1,1'-thiocarbonyldiimidazole was added, and the mixture was stirred at room temperature for 64 hours. The solvent was distilled off and the residue was washed with chloroform/ether to give 1.16 g of the desired product (68.5% yield, pale brown crystals).

Workup

  1. distillationThe solvent was distilled off
  2. washthe residue was washed with chloroform/ether

Sources & evidence

ORD record
ord-60d992e5f70047c985ad708eb5f4a3b2
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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