Pyridine → 1-[2-Chloro-4-(3-chlorophenoxy)phenoxy]-2-[N-ethyl-N-(4-chlorophenylsulfenyl)aminocarbonyloxy]ethane
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]Cl)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[Cl:17][C:18]1[CH:32]=[C:31]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=2)[CH:30]=[CH:29][C:19]=1[O:20][CH2:21][CH2:22][O:23][C:24]([NH:26][CH2:27][CH3:28])=[O:25].N1C=CC=CC=1>CCOCC>[Cl:17][C:18]1[CH:32]=[C:31]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=2)[CH:30]=[CH:29][C:19]=1[O:20][CH2:21][CH2:22][O:23][C:24]([N:26]([CH2:27][CH3:28])[S:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2 g of 4-chlorophenylsulfenyl chloride in 1 0 ml of toluene is added dropwise with stirring at 0°-5° C. in the course of approximately 30 minutes to a mixture of 3.7 g of 1-[2-chloro-4-(3-chlorophenoxy)phenoxy]2-ethylaminocarbonyloxyethane, 10 ml of pyridine and 10 ml of toluene, and stirring is continued for 16 hours at room temperature. The reaction mixture is diluted with 100 ml of ether, washed three times using ice-cold 1N hydrochloric acid and three times using water, the organic phase is dried over sodium sulfate and the solvent is evaporated in vacuo. The crude product is purified on silica gel using diethyl ether/n-hexane (1:3) as mobile phase. This gives the title compound of refractive index nD20 1.6209.
Workup
- washwashed three times
- dry with materialthe organic phase is dried over sodium sulfate
- customthe solvent is evaporated in vacuo
- customThe crude product is purified on silica gel
Sources & evidence
- ORD record
- ord-f3ec063891e54068a8275cf34cb46b2c
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05648494
Reaction notes
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