Ammonia → 1-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea

HRID 1803176Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][C:11]([CH3:14])=[N:10]1)[NH2:5].[C:15](N1C=CC=CC1=O)([N:17]1C=CC=CC1=O)=[S:16].N>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:15]([NH2:17])=[S:16])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][C:11]([CH3:14])=[N:10]1

Participants

Conditions

Temperature: -20 °C

Procedure

Step S (3): Dichloromethane (125 mL) was added to a flask charged with 3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (5.00 g, 26.0 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (6.65 g, 28.6 mmol). The crude reaction was concentrated in vacuo. Methanolic ammonia (2.0 M, 150 mL, 300 mmol) was added at rt to the dark-red solid residue. A light brown precipitate resulted. After stirring for 30 min, the crude reaction mixture was chilled in a −20° C. freezer for 1 h. The solid precipitate was collected using vacuum filtration. The solid was rinsed with cold methanol and dried under high vacuum to afford 1-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)thiourea (5.48 g, 84% yield) as an off-white solid. LC-MS (M+H)+ 252.2. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.02 (br. s., 1 H), 8.80 (d, J=2.1 Hz, 1 H), 7.91 (dd, J=13.4, 2.1 Hz, 1 H), 7.66 (t, J=8.7 Hz, 1 H), 7.33 (dd, J=8.4, 2.0 Hz, 1 H), 2.36 (s, 3 H).

Workup

customThe crude reaction
concentrationwas concentrated in vacuo
customA light brown precipitate resulted
customthe crude reaction mixture
customThe solid precipitate was collected
filtrationvacuum filtration
washThe solid was rinsed with cold methanol
customdried under high vacuum

Sources & evidence

ORD record: ord-90771934096a4686b3604163c5215ada
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

Loading…