4-Fluorobenzonitrile → HCID 178510104, compound

HRID 1698489Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[Na].[SH:11][C:12]1[N:13]=[N:14][NH:15][CH:16]=1>CN(C)C=O>[NH:15]1[CH:16]=[C:12]([S:11][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[N:13]=[N:14]1

Participants

Conditions

Temperature: 125 °C

Procedure

To 4-fluorobenzonitrile (6.1 g) in dry N,N-dimethylformamide (50 mL), under nitrogen, was added 4-mercapto-1,2,3-triazole sodium salt (6.2 g), and the stirred mixture heated in an oil bath at 125° C. for 18 h. The mixture was cooled to room temperature, and most of the solvent stripped at reduced pressure. The residue was partitioned between ethyl acetate and water, the organic phase washed with water, brine, then dried (sodium sulphate), and solvent stripped at reduced pressure. The residue was azeotroped with toluene, and the resulting solid triturated with isohexane, collected by filtration, washed with cold toluene, then isohexane, and dried in vacuo to give the title compound as a yellow solid (8.4 g). 1H NMR (360 MHz, CDCl3) δ 12.45 (1H, br s), 7.92 (1H, s), 7.51 (2H, d, J=8.5 Hz), 7.22 (2H, d, J=8.5 Hz).

Workup

temperatureThe mixture was cooled to room temperature
customThe residue was partitioned between ethyl acetate and water
washthe organic phase washed with water, brine
dry with materialdried (sodium sulphate), and solvent
customThe residue was azeotroped with toluene
customthe resulting solid triturated with isohexane
filtrationcollected by filtration
washwashed with cold toluene
dry with materialisohexane, and dried in vacuo

Sources & evidence

ORD record: ord-aadbb865461d4a65a4a9bde72e225ecc
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163956B2

Reaction notes

Loading…