Lawesson's reagent → Ethyl 2-(2,6-dichloropyridin-3-ylamino)-2-thioxoacetate
Reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:16])[N:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([NH:8][C:9](=[S:26])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:16])[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of ethyl 2-(2,6-dichloropyridin-3-ylamino)-2-oxoacetate (48.92 g, 186.0 mmol) in toluene (380 mL) was added Lawesson's Reagent (75.21 g, 186.0 mmol), and the resulting suspension was stirred at 90° C. for 4 h. The reaction mixture was then cooled to room temperature and filtered through Celite™, washing with 300 mL toluene. The combined filtrates were concentrated in vacuo at 40° C., and the residue was taken up in CH2Cl2 (200 mL) and filtered through a 200 g pad of silica gel, washing with additional CH2Cl2 (4×150 mL). The filtrate was concentrated in vacuo to afford ethyl 2-(2,6-dichloropyridin-3-ylamino)-2-thioxoacetate as an orange solid.
Workup
- temperatureThe reaction mixture was then cooled to room temperature
- filtrationfiltered through Celite™
- washwashing with 300 mL toluene
- concentrationThe combined filtrates were concentrated in vacuo at 40° C.
- filtrationfiltered through a 200 g pad of silica gel
- washwashing with additional CH2Cl2 (4×150 mL)
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-f74ad389b6fc44929621fb24892329ce
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842685B2
Reaction notes
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