Pyridine → 2-chloro-N-cyclopropyl-4-iodobenzamide
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[N:16]1[CH:21]=[CH:20][CH:19]=CC=1.C1(N)CC1>C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:16][CH:21]1[CH2:19][CH2:20]1)=[O:6]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
2-Chloro-4-iodobenzoic acid (3.31 g, 11.7 mmol) was dissolved in ethyl acetate (23 ml), admixed with one drop of N,N-dimethylformamide and thionyl chloride (6.96 g, 59.0 mmol), and heated under reflux overnight. The cooled suspension was concentrated under reduced pressure and taken up in dichloromethane (60 ml). The solution was cooled to 0° C., and pyridine (925 mg, 11.7 mmol) and cyclopropylamine (668 mg, 11.7 mmol) were added dropwise. The reaction mixture was warmed up to room temperature and stirred overnight. Then it was washed with hydrochloric acid (1 M), dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure.
Workup
- temperatureheated
- temperatureunder reflux overnight
- concentrationThe cooled suspension was concentrated under reduced pressure
- temperatureThe reaction mixture was warmed up to room temperature
- washThen it was washed with hydrochloric acid (1 M)
- dry with materialdried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-4c1b729243024bd78ee6d3a6d9a3b084
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710242B2
Reaction notes
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