Triethylamine → [5-Phenyl-4-(3-pyridyl)-1,3-thiazol-2-yl]amine

HRID 1167654Notes

Reaction equation

Br.Br[CH:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=O.[NH2:18][C:19]([NH2:21])=[S:20].C(N(CC)CC)C>C(#N)C>[C:12]1([C:3]2[S:20][C:19]([NH2:21])=[N:18][C:4]=2[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-bromo-2-phenyl-1-(3-pyridyl)ethanone hydrobromide (2.00 g) and thiourea (432 mg) in acetonitrile (30 mL), was added triethylamine (0.80 mL) dropwise and the resulting mixture was stirred at 80° C. for 3 h. The solvent was removed under reduced pressure and an aqueous saturated solution of sodium hydrogen carbonate was added to the residue. The mixture was extracted with ethyl acetate. The organic phases were washed with water, dried and concentrated under reduced pressure to give the amorphous title compound (1.10 g, yield 84%).

Workup

customThe solvent was removed under reduced pressure
additionan aqueous saturated solution of sodium hydrogen carbonate was added to the residue
extractionThe mixture was extracted with ethyl acetate
washThe organic phases were washed with water
customdried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f82e8a8b3c1e4421941e83bc23fadfea
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620825B1

Reaction notes

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