Lawesson's reagent → Isopropyl 7-(3-chlorophenyl)-3-thioxo-3,4-dihydroquinoxaline-1(2H)-carboxylate

HRID 1007116Notes

Reaction equation

HRID 1007116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([NH:12][C:13](=O)[CH2:14][N:15]3[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([NH:12][C:13](=[S:34])[CH2:14][N:15]3[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 22667742isopropyl 7-(3-chlorophenyl)-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate

Product 1

HCID 22667725Isopropyl 7-(3-chlorophenyl)-3-thioxo-3,4-dihydroquinoxaline-1(2H)-carboxylate

Procedure

Prepared according to the procedure for Example 24 from isopropyl 7-(3-chlorophenyl)-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate and Lawesson's reagent. A yellowish solid: m.p. 208-212° C.; 1H-NMR (DMSO-d6) δ 1.27 (d, J=6.1 Hz, 6H), 4.62 (s, 2H), 4.94 (sep, J=6.1 Hz, 1H), 7.23 (m, 4H), 7.64 (t, J=1.8 Hz, 1H), 7.90 (s, 1H), 12.80 (s, 1H), MS (ESI) m/z 359/361 (M−H)-.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-179cd13c8e754809b21d52be95a70ce2
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Reaction notes

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