Hydrochloric Acid → N-(3-methyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide
Reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1([C:9]([OH:11])=O)[CH2:8][CH2:7]1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH:21]([F:23])[F:22])[NH2:16].Cl>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:12][C:13]1[CH:14]=[C:15]([NH:16][C:9]([C:6]2([CH3:5])[CH2:8][CH2:7]2)=[O:11])[CH:17]=[CH:18][C:19]=1[O:20][CH:21]([F:22])[F:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of toluene (50 ml) and pyridine (4.2 g) cooled at 0° C., thionyl chloride (1.3 g) was added, and a solution of 1-methylcyclopropanecarboxylic acid (1.0 g) in toluene was dropwise added thereto while stirring. A solution of 3-methyl-4-difluoromethoxyaniline (1.75 g) in toluene was dropwise added thereto. After the dropwise addition was completed, stirring was continued at room temperature for 3 hours. The reaction mixture was admixed with 5% hydrochloric acid (20 ml). The organic solvent layer was separated, washed with 1% sodium hydroxide solution and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give crude crystals (2.2 g). The crude crystals were recrystallized from ethanol to give N-(3-methyl-4-difluoromethoxyphenyl)-1-methylcyclopropanecarboxamide (1.8 g). M.P., 68°-69° C.
Workup
- additionAfter the dropwise addition
- stirringstirring
- customThe organic solvent layer was separated
- washwashed with 1% sodium hydroxide solution and saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customto give crude crystals (2.2 g)
- customThe crude crystals were recrystallized from ethanol
Sources & evidence
- ORD record
- ord-9df445b6a1e14df4b8755eb4f62f3a7e
- Source dataset
- uspto-grants-1984_05
- Patent number
- US04447260
Reaction notes
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