Oxalyl chloride → 4-(N,N-diethylaminomethyl)benzoyl chloride hydrochloride
Reaction equation
[ClH:1].[CH2:2]([N:4]([CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=1)[CH2:5][CH3:6])[CH3:3].C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl>[ClH:20].[CH2:2]([N:4]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([Cl:1])=[O:13])=[CH:15][CH:16]=1)[CH2:5][CH3:6])[CH3:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a well-stirred suspension consisting of 1.34 g. (5.0 mmole) of 4-(N,N-diethylaminomethyl)benzoic acid hydrochloride (the product of Preparation G) in 25 ml. of methylene chloride under a nitrogen atmosphere, there was added over a five-minute period a solution consisting of 1.5 g. (0.0118 mole) of oxalyl chloride dissolved in 5 ml. of methylene chloride. The resulting reaction mixture was refluxed for a period of 17 hours and then cooled to room temperature (~20° C.). The colorless solution so obtained was evaporated under reduced pressure, and the resulting residue was washed twice with methylene chloride and then stripped free of solvent to give a white solid product. In this way, there was readily obtained substantially pure 4-(N,N-diethylaminomethyl)benzoyl chloride hydrochloride, which was used in the next reaction step without any further purification being necessary. The yield of product was assumed to be quantitative.
Workup
- customThe resulting reaction mixture
- temperaturewas refluxed for a period of 17 hours
- customThe colorless solution so obtained
- customwas evaporated under reduced pressure
- washthe resulting residue was washed twice with methylene chloride
- customto give a white solid product
Sources & evidence
- ORD record
- ord-56123fedfe2048a2b710b8e347bbfc82
- Source dataset
- uspto-grants-1986_11
- Patent number
- US04623486
Reaction notes
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