Thionyl Chloride → HCID 54165256, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][N:10]([CH2:19][C:20]([OH:22])=[O:21])[C:9]2=[O:23])=[CH:4][CH:3]=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH2:6]([O:21][C:20](=[O:22])[CH2:19][N:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]1=[O:23])[CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
1 g of [3-(4-chlorophenyl)-2-oxo-4-phenyl-4-imidazolin-1-yl] acetic acid are dissolved in a small amount of anhydrous chloroform. 0.7 g of thionylchloride are added thereto and the mixture is stirred at about 50° C. for 2 hours. The mixture is evaporated in a vacuum, the residue is mixed with a small amount of chloroform and 0.31 g of hexanol are added to the mixture. After stirring for one hour at room temperature, the CHCl3 -solution is first extracted with an NaHCO3 -solution and then with water. It finally is dried over Na2SO4. The CHCl3 -solution is evaporated, remaining hexanol is distilled off a high vacuum and the residue is further purified chromatographically on silicic acid gel using CHCl3 as eluant.
Workup
- customThe mixture is evaporated in a vacuum
- additionthe residue is mixed with a small amount of chloroform and 0.31 g of hexanol
- additionare added to the mixture
- stirringAfter stirring for one hour at room temperature
- extractionthe CHCl3 -solution is first extracted with an NaHCO3 -solution
- dry with materialIt finally is dried over Na2SO4
- customThe CHCl3 -solution is evaporated
- distillationis distilled off a high vacuum
- customthe residue is further purified chromatographically on silicic acid gel
Sources & evidence
- ORD record
- ord-7d27a07bc68f40fb8e10d982a4e5de06
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04349684
Reaction notes
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