Dimethylformamide dimethyl acetal → HCID 54166861, compound

HRID 1459731Notes

Reaction equation

HRID 1459731 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:3]=1.CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>CN(C)C=O>[CH3:18][N:19]([CH3:21])[CH:20]=[CH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 542579534-Methyl-5-nitro-2-(1H-1,2,4-triazol-1-yl)pyridine

Product 1

HCID 54166861HCID 54166861, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-methyl-5-nitro-2-(1,2,4-triazol-1-yl)pyridine (4.1 g, 20 mmol) in dry dimethylformamide (30ml) was added dimethylformamide dimethyl acetal (5.9ml, 44 mmol) and the mixture heated at 90° C. for 20 min. The solvent was evaporated in vacuo using toluene as an azeotrope to give the title compound (5.2 g, 100%) as a dark red solid; mp 225°-228° C. 1H NMR (360 MHz, CDCl3) δ 3.10 (6H, s), 6.13 (1H, J=13.1 Hz), 7.54 (1H, J=13.1 Hz), 7.81 (1H, s), 8.04 (1H, s), 8.92 (1H, s), 9.17 (1H, s).

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-2908feee34784696abae4acb11cea5c4
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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