Dimethylamine → 3-(chloromethyl)-N,N-dimethylbenzamide
Reaction equation
[CH3:1][NH:2][CH3:3].CCN(CC)CC.[Cl:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17]>C(Cl)Cl>[Cl:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([N:2]([CH3:3])[CH3:1])=[O:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of dimethylamine (2.91 mL, 5.82 mmol, 2.0M THF), NEt3 (0.885 mL, 6.35 mmol) and CH2Cl2 30 mL was cooled to 0° C. 3-(Chloromethyl)benzoyl chloride (1.0 g, 5.29 mmol) was added as a CH2Cl2 solution (3 mL) and the solution was stirred at 0° C. for 2 hours and then at ambient temperature for 2 hours. The reaction was washed with 1N HCl followed by brine, and the organic layer was dried over Na2SO4, filtered and concentrated. The product was purified by column chromatography (EtOAc) to provide 0.745 g (71%) of the product as colorless oil.
Workup
- waitat ambient temperature for 2 hours
- washThe reaction was washed with 1N HCl
- dry with materialthe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe product was purified by column chromatography (EtOAc)
Sources & evidence
- ORD record
- ord-493d0501f551417882496be2877a7143
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174981B2
Reaction notes
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