Water → N-(pyridin-2-yl)-5-thiocyanatothiazol-2-amine

HRID 1685294Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][CH:10]=[CH:11][N:12]=1.[S-:13][C:14]#[N:15].[Na+].BrBr.O>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([S:13][C:14]#[N:15])=[CH:11][N:12]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a suspension of N-(pyridin-2-yl)thiazol-2-amine (4.26 g, 24 mmol) and sodium thiocyanate (3.9 g, 48 mmol, 2 eq) in methanol (100 mL) at 0° C., was slowly added bromine (1.23 mL, 24 mmol, 1 eq) over 2 min, then the temperature was raised to 23° C. and the mixture was stirred for 3 h. The resulting suspension was added to stirring cold water (400 mL) and the resulting precipitate was collected by filtration and vacuum dried (4.5 g, 80%). 1H NMR (400 MHz, DMSO-D6) δ ppm 7.00-7.08 (1H, m), 7.11 (1H, d, J=8.34 Hz), 7.74-7.84 (1H, m), 7.89 (1H, s), 8.39 (1H, d, J=5.05 Hz), 11.93 (1H, s). LC/MS (M+H)+: 235.

Workup

customover 2 min
additionThe resulting suspension was added
filtrationthe resulting precipitate was collected by filtration and vacuum
customdried (4.5 g, 80%)

Sources & evidence

ORD record: ord-c67333b50af747259fed56de331ba77a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148400B2

Reaction notes

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