Hydrazine hydrate (1:1) → 1-[4-(2-Fluorophenyl)-5-(phenylthio)-1,3-thiazol-2-yl]methanamine

HRID 2194727Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)[S:11][C:12]=1[S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.NN.C(=O)([O-])O.[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:20][NH2:21])[S:11][C:12]=1[S:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-{[4-(2-fluorophenyl)-5-(phenylthio)-1,3-thiazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione (345 mg) in ethanol (5 mL) was added hydrazine monohydrate (0.05 mL) and the mixture was stirred at 70° C. for 3 hr. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 209 mg, yield 86%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e69d183b6d4448ed93df533b77d649ca
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334301B2

Reaction notes

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