Ammonia → 7-Bromo-5-pyrazol-1-yl-benzothiazol-2-ylamine

HRID 447015Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:13][C:14]([NH2:16])=[S:15])[CH:5]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:7]=1.BrBr.N>C(Cl)Cl.O>[Br:1][C:2]1[C:3]2[S:15][C:14]([NH2:16])=[N:13][C:4]=2[CH:5]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3-bromo-5-pyrazol-1-yl-phenyl)-thiourea (1.0 g, 3.0 mmol) in DCM (17.0 mL) at 0° C. was added dropwise a solution of Br2 (1.07 g, 6.0 mmol, in 3.0 ml of DCM) over a period of 15 min. The reaction mixture was stirred at 0° C. for 15 min followed by refluxing for 2 h. The reaction mixture was cooled to room temperature and filtered to get the crude residue that was washed with hexane and diethyl ether. The solid thus obtained was dissolved in H2O, basified with aqueous ammonia solution to pH 10-12 and extracted with ethyl acetate (×3). The combined organic was washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (230-400 M, 25% EtOAc-Hexane) to get the desired product (0.30 g, 30%).

Workup

temperatureby refluxing for 2 h
temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
customto get the crude residue that
washwas washed with hexane and diethyl ether
customThe solid thus obtained
extractionextracted with ethyl acetate (×3)
washThe combined organic was washed with water
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified over silica gel (230-400 M, 25% EtOAc-Hexane)

Sources & evidence

ORD record: ord-11fe587a16654129a22189c79c234f8e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481544B2

Reaction notes

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