Bromine → 5-bromo-N-(pyridin-2-yl)thiazol-2-amine

HRID 1685293Notes

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.[Br:13]Br.OS([O-])=O.[Na+]>C(Cl)(Cl)Cl>[Br:13][C:10]1[S:9][C:8]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:12][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of N-(pyridin-2-yl)thiazol-2-amine (9.76 g, 55.07 mmol) in degassed chloroform (180 mL) was added bromine (3.11 mL, 60.6 mmol, 1.1 eq) at 23° C. The reaction was stirred for 15 minutes and followed by LC/MS. Bromine (2×0.3 mL) was added until reaction completed. The mixture was cooled down to 0° C. and 10% aq. NaHSO3 (150 mL) was added. The suspension changed color and the solid was filtered, washed with water and vacuum dried overnight. The title compound was obtained as a solid (10.79 g, 77%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.94-6.99 (1H, m), 7.04 (1H, d, J=8.34 Hz) 7.45 (1H, s), 7.74 (1H, td, J=7.83, 1.77 Hz), 8.31 (1H, d, J=5.31 Hz), 11.54 (1H, s). LC/MS (M+H)+: 256, 258; (M−H)−: 254, 256.

Workup

filtrationthe solid was filtered
washwashed with water and vacuum
customdried overnight

Sources & evidence

ORD record: ord-b2c06d77bc9c40a18e5b3dbc0d4d8795
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148400B2

Reaction notes

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