Bromomethylcyclopropane → 0-Cyclopropylmethyl (2,6-dichlorophenyl)acetamidoxime
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10](=[N:12][OH:13])[NH2:11].[CH:14]1([CH2:17]Br)[CH2:16][CH2:15]1.CC(C)([O-])C.[K+].P([O-])(O)(O)=O.[Na+]>CN(C)C=O>[CH:14]1([CH2:17][C:4]2([Cl:8])[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]2[CH2:9][C:10](=[N:12][OH:13])[NH2:11])[CH2:16][CH2:15]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
10.0 g (46 mmol) of (2,6-dichlorophenyl)acetamidoxime in 40 ml of dimethylformamide were admixed with 6.5 g (48 mmol) of cyclopropylmethyl bromide. The mixture was cooled to −20° C. and admixed dropwise with 5.4 g (48 mmol) of potassium tert-butoxide in 20 ml of dimethylformamide. The mixture was stirred at −20° C. for 1 h and then at room temperature overnight, poured into aqueous sodium dihydrogen phosphate buffer (pH 6) and extracted 5 times with diethyl ether. The combined extracts were washed twice with water and once with saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. Yield: 12.3 g of a yellow oil which was reacted further without any further purification.
Workup
- extractionextracted 5 times with diethyl ether
- washThe combined extracts were washed twice with water and once with saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customYield: 12.3 g of a yellow oil which was reacted further without any further purification
Sources & evidence
- ORD record
- ord-f1af577398d34c7e9d80b35139659b9f
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101900B2
Reaction notes
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