Thionicotinamide → 4-(2-Hydroxyphenyl)-2-(3-pyridyl)thiazole

HRID 366438

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=O)[CH2:12]Br)(=O)C.[C:15]([NH2:23])(=[S:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1>CC(C)=O>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15]2[S:22][CH:12]=[C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[OH:4])[N:23]=2)[CH:17]=1

Participants

Conditions

Temperature: 20 °C

Procedure

o-(Bromoacetyl)phenyl acetate (2.57 g, 10 mmol) in dry acetone (30 mL) was treated with thionicotinamide (1.38 g, 10 mmol). The mixture was refluxed 16 hours, cooled to about 20° C. at which point a precipitate formed (2.46 g). The precipitate was filtered and dried in vacuo. The precipitate was dissolved in MeOH (50 mL) and treated with 10% NaOH in H2O (20 mL) for 1 hour at about 20° C. to hydrolyze the acetate ester. The pH was adjusted to neutrality with 6N HCl while chilling on ice/H2O and the volume was reduced to about 35 mL in vacuo. After cooling to about 4° C., an orange solid precipitate formed, which was removed by filtration and dried in vacuo to constant mass to yield 36-50% product (LSIMS m/s 254 (MH+)).

Workup

temperatureThe mixture was refluxed 16 hours
customformed (2.46 g)
filtrationThe precipitate was filtered
customdried in vacuo
dissolutionThe precipitate was dissolved in MeOH (50 mL)
additiontreated with 10% NaOH in H2O (20 mL) for 1 hour at about 20° C.
temperaturewhile chilling on ice/H2O
temperatureAfter cooling to about 4° C.
customan orange solid precipitate formed
customwhich was removed by filtration
customdried in vacuo to constant mass

Sources & evidence

ORD record: ord-2df6a646106e4179ad26bb85ef0ba612
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130217

Linked notes

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