2-Acetamido-5-aminopyridine → N-(6-acetylamino-3-pyridyl)-N'-(1,2,2-trimethylpropyl)thiourea

HRID 257430Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][N:6]=1)(=[O:3])[CH3:2].[CH3:12][CH:13]([N:18]=[C:19]=[S:20])[C:14]([CH3:17])([CH3:16])[CH3:15]>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[N:6]=[CH:7][C:8]([NH:11][C:19]([NH:18][CH:13]([CH3:12])[C:14]([CH3:17])([CH3:16])[CH3:15])=[S:20])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-acetylamino-5-aminopyridine (150 mg, 0.99 mmol) in pyridine (1.5 ml), 213 mg (1.49 mmol) of 1,2,2-trimethylpropyl isothiocyanate was added dropwise, followed by stirring at room temperature for 22 hours, at 50° C. for 5 hours and further at room temperature for 15 hours. Then, the solvent was removed by distillation under reduced pressure. The residue was recrystallized from chloroform-hexane to obtain 232 g of the intended product as a flesh-colored powder (yield: 79%).

Workup

customThen, the solvent was removed by distillation under reduced pressure
customThe residue was recrystallized from chloroform-hexane

Sources & evidence

ORD record: ord-f857ef72f076470ebebe7dea6087284e
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262415

Reaction notes

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