Lawesson's reagent → 4-Chloro-3,5-bis(trifluoromethyl)benzothioamide
Reaction equation
[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:5]([C:6](=[S:28])[NH2:8])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 4-chloro-3,5-bis(trifluoromethyl)benzamide (1.2 g) in toluene (20 mL) was added Lawesson's reagent (3.32 g, 2.0 eq.). The reaction mixture was stirred at 90° C. for 8 h before being cooled to room temperature and filtered. The filtrate was poured into water and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine (3×50 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure (25° C., 20 mmHg) to afford 2 g of crude compound. The crude compound was purified by combi-flash chromatography (eluting with 7% EtOAc:hexane) to afford 1.0 g of desired compound (yield: 79%).
Workup
- temperaturebefore being cooled to room temperature
- filtrationfiltered
- additionThe filtrate was poured into water
- extractionextracted with EtOAc (3×100 mL)
- washThe combined organic extracts were washed with brine (3×50 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure (25° C., 20 mmHg)
- customto afford 2 g of crude compound
- customThe crude compound was purified by combi-flash chromatography (eluting with 7% EtOAc:hexane)
Sources & evidence
- ORD record
- ord-b909c663450b49d6bf8f4d74c0937d47
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206158B2
Reaction notes
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