Thionyl Chloride → N-(4-(1-chloroethyl)phenylmethyl)acetamide
Reaction equation
O[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:3].S(Cl)([Cl:17])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:17][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
To a solution of N-(4-(1-hydroxyethyl)phenylmethyl)acetamide (5.26 g) in chloroform (40 ml) was added dropwise a solution of thionyl chloride (2.1 ml) in chloroform (10 ml) at below 5° C. over 20 min. The mixture was stirred at 30° C. for 1 hr. The mixture was poured into a saturated sodium hydrogencarbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (elution solvent; methanol:chloroform=4:96) to give the title compound (4.08 g) as white crystals.
Workup
- extractionextracted with chloroform
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated
- customThe obtained residue was purified by silica gel column chromatography (elution solvent; methanol:chloroform=4:96)
Sources & evidence
- ORD record
- ord-942abe6408a74c4082bf59132c2ae5c8
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455528B1
Reaction notes
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