Water → 2,6-dichloro-N-(2-chloroethyl)benzamide
Reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH2:5].C(=O)([O-])[O-].[K+].[K+].O.[Cl:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:15]=1[C:16](Cl)=[O:17]>ClCCl>[Cl:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:15]=1[C:16]([NH:5][CH2:4][CH2:3][Cl:2])=[O:17]Participants
Procedure
To a stirred (vigourously) mixture of 17.4 parts of 2-chloroethanamine hydrochloride, 20.7 parts of potassium carbonate and 225 parts of water was added dropwise a mixture of 31.3 parts of 2,6-dichlorobenzoyl chloride and 120 parts of dichloromethane at room temperature: slightly exothermic reaction. Upon completion, stirring at room temperature was continued for one hour. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with water, dried, filtered and evaporated. The residue was crystallized from methylbenzene. The product was filtered off and dried, yielding 25.8 parts (68.8%) of 2,6-dichloro-N-(2-chloroethyl)benzamide; mp. 113.8° C. (intermediate 30).
Workup
- additionwas added dropwise
- customslightly exothermic reaction
- stirringUpon completion, stirring at room temperature
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with dichloromethane
- washThe combined organic phases were washed with water
- customdried
- filtrationfiltered
- customevaporated
- customThe residue was crystallized from methylbenzene
- filtrationThe product was filtered off
- customdried
Sources & evidence
- ORD record
- ord-b90cb27282c6471eaa352cb74f4e6f51
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04962115
Reaction notes
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