Acetone → (6-Bromo-pyridin-2-YL)thiourea

HRID 929662Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([NH:11]C(=O)C2C=CC=CC=2)=[S:10])[CH:5]=[CH:4][CH:3]=1.CC(C)=O.[OH-].[Na+]>CO>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([NH2:11])=[S:10])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

4.933 g (14.67 mmol) N-{[(6-bromopyridin-2-yl)amino]carbonothioyl}benzamide was suspended in 40 mL methanol and additionally combined with 7 mL acetone. After addition of 1 N sodium hydroxide solution (40.0 mmol) the reaction mixture became completely clear with a light brown color. The mixture was heated for 40 min at 65° C. (oil bath temperature) and then stirred for 1 hr at room temperature. A solid crystallized out. The organic solvent was removed under vacuum, and after cooling on an ice bath the solid was filtered off and washed with water. The solid was dried over phosphorus pentoxide in a dessicator under high vacuum (4×10 mbar). The desired product N-(6-bromopyridin-2-yl)thiourea was obtained in the form of colorless needles in a yield of 3.158 g (13.61 mmol, 93%).

Workup

customA solid crystallized out
customThe organic solvent was removed under vacuum
temperatureafter cooling on an ice bath the solid
filtrationwas filtered off
washwashed with water
dry with materialThe solid was dried over phosphorus pentoxide in a dessicator under high vacuum (4×10 mbar)

Sources & evidence

ORD record: ord-453275f6e3824467b76a85920ac3bcba
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296697B2

Reaction notes

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