1,1'-Thiocarbonyldi-2(1H)-pyridone → 2-Isothiocyanato-6-methoxy-[1,2,4]triazolo[1,5-a]pyridine

HRID 1875886Notes

Reaction equation

HRID 1875886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([N:9]=[C:10]([NH2:12])[N:11]=2)[CH:8]=1.[C:13](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:14]>ClCCl>[N:12]([C:10]1[N:11]=[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][N:7]2[N:9]=1)=[C:13]=[S:14]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 468640666-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 574765522-Isothiocyanato-6-methoxy-[1,2,4]triazolo[1,5-a]pyridineYield 44.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.3 g, 1.8 mmol) in dichloromethane (15 mL) was added 1,1′-thiocarbonyldi-2(1H)-pyridone (0.51 g, 2.2 mmol). The reaction was stirred at room temperature overnight, concentrated in vacuo and purified via flash chromatography yielding 2-isothiocyanato-6-methoxy-[1,2,4]triazolo[1,5-a]pyridine (166 mg, 0.8 mmol, 44% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 8.03 (1H, d, J=2.20 Hz), 7.54 (1H, d, J=9.88 Hz), 7.34 (1H, dd, J=9.51, 2.56 Hz), 3.88 (3H, s).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified via flash chromatography

Sources & evidence

ORD record
ord-c30a880185174780a0f41039dafb725e
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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