Benzene → N-(1-Methylethyl)-3-Chlorocinnamoylcarboxamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=O.S(Cl)(Cl)=[O:14].[CH:17]([NH2:20])(C)C.[CH:21]1[CH:26]=CC=C[CH:22]=1>>[CH3:22][CH:21]([NH:20][C:17]([C:7](=[O:9])[CH:6]=[CH:5][C:4]1[CH:10]=[CH:11][CH:12]=[C:2]([Cl:1])[CH:3]=1)=[O:14])[CH3:26]Participants
Procedure
A mixture of 3-chlorocinnamic acid (25 g.), thionyl chloride (19.4 g.) and benzene (300 ml.) was heated under reflux for 2 hours, then evaporated under reduced pressure on a rotary evaporator to give an oil. The oil was dissolved in benzene (50 ml.), and the benzene solution was added slowly to a mixture of isopropylamine (25 g.) and benzene (300 ml.). The resulting mixture was allowed to stir at room temperature for 2 hours, and heated under mild reflux for 1 hour. It was then allowed to set at room temperature overnight. The precipitate thus separated was collected on a filter, and washed with benzene. The combined filtrate and washings were washed with water, then dried over potassium carbonate. Removal of benzene under reduced pressure on a rotary evaporator gave an oil which solidified on standing. The product melted at 92°-94°, and weighed 28 g.
Workup
- temperaturewas heated
- temperatureunder reflux for 2 hours
- customevaporated under reduced pressure on a rotary evaporator
- customto give an oil
- temperatureheated
- temperatureunder mild reflux for 1 hour
- waitto set at room temperature overnight
- customThe precipitate thus separated
- customwas collected on a filter
- washwashed with benzene
- washThe combined filtrate and washings were washed with water
- dry with materialdried over potassium carbonate
- customRemoval of benzene under reduced pressure
- customon a rotary evaporator
- customgave an oil which
Sources & evidence
- ORD record
- ord-5393712a80814cc2a34af483003e0910
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04401832
Reaction notes
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