Dimethylformamide → Diethylthiocarbamic acid O-quinoxalin-5-yl ester

HRID 2265181Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH2:23]([N:25]([CH2:29][CH3:30])[C:26](Cl)=[S:27])[CH3:24]>O>[N:7]1[C:8]2[C:3](=[C:2]([O:1][C:26](=[S:27])[N:25]([CH2:29][CH3:30])[CH2:23][CH3:24])[CH:11]=[CH:10][CH:9]=2)[N:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 5-hydroxyquinoxaline (2.13 g, 14.6 mmol), finely ground K2CO3 (4.0 g, 29 mmol), and DMF (50 mL) was stirred at 23° C. for 1 h. Solid diethylthiocarbamoyl chloride (2.43 g, 16.1 mmol) was then added. The resulting mixture was stirred for 2 h, then was diluted with water (150 mL) and extracted with Et2O (2×100 mL). The combined organic extracts were washed with water (100 mL) and brine (100 mL), then dried and concentrated to a viscous orange oil, which was used without purification (3.63 g, 95%). MS (ESI+): mass calcd. for C13H15N3OS, 261.1; m/z found, 262 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.85-8.65 (m, 2H), 7.96 (dd, J=8.5, 1.1, 1H), 7.71 (t, J=7.9, 1H), 7.46 (dd, J=7.6, 1.2, 1H), 3.87 (q, J=7.1, 2H), 3.78 (q, J=7.1, 2H), 1.38 (t, J=7.1, 3H), 1.28 (t, J=7.1, 3H). 13C NMR (125 MHz, CDCl3): 186.6, 149.4, 144.9, 144.5, 143.4, 137.0, 128.9, 127.0, 123.1, 48.2, 44.5, 13.1, 11.5.

Workup

stirringThe resulting mixture was stirred for 2 h
extractionextracted with Et2O (2×100 mL)
washThe combined organic extracts were washed with water (100 mL) and brine (100 mL)
customdried
concentrationconcentrated to a viscous orange oil, which
customwas used without purification (3.63 g, 95%)

Sources & evidence

ORD record: ord-7a1dd7d0fde64828bf32d58929c81c15
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855292B2

Reaction notes

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