Toluene → 2-Methylcyclohexyl 2-chloro-5[(phenylthiomethyl)amino]benzoate
Reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=O)C2C=CC=CC=2)=[CH:14][C:3]=1[C:4]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[CH3:13])=[O:5].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1.C(=O)(O)[O-].[Na+].[C:54]1(C)[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][S:36][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[CH:14][C:3]=1[C:4]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[CH3:13])=[O:5]Participants
Procedure
To a solution of 2-methylcyclohexyl 2-chloro-5-(benzoylamino)benzoate (1.8 g, 0.0048 mole) in toluene (100 ml) was added Lawesson's Reagent (2.5 g), sodium bicarbonate (1.0 g) to produce the reaction mixture. The reaction mixture was stirred and refluxed for 4 hours. The reaction mixture was then cooled to ambient temperature which resulted in the formation of a white solid precipitate. The white solid was filtered off. The filtrate was then passed through a short column of aluminum oxide (neutral) using ether/hexane as eluent to give a yellow solution. The yellow solution was concentrated and a yellow solid crystallized. The yellow solid was filtered to give 2-methylcyclohexyl 2-chloro-5[(phenylthiomethyl)amino]benzoate as a yellow solid (1.3 g, m.p. 143°-144° C.).
Workup
- customto produce the reaction mixture
- temperaturerefluxed for 4 hours
- customresulted in the formation of a white solid precipitate
- filtrationThe white solid was filtered off
- customto give a yellow solution
- concentrationThe yellow solution was concentrated
- customa yellow solid crystallized
- filtrationThe yellow solid was filtered
Sources & evidence
- ORD record
- ord-31d5a0b6619c44e6b0fd7fd759580367
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05756813
Reaction notes
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