N,N-Diethylaniline → 2-Chlorocycloheptimidazole
Reaction equation
O[C:2]1[N:3]=[C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=[C:5]2[N:6]=1.P(Cl)(Cl)([Cl:14])=O.C(N(CC)C1C=CC=CC=1)C.C(=O)([O-])O.[Na+]>>[Cl:14][C:2]1[N:3]=[C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=[C:5]2[N:6]=1Participants
Conditions
- Temperature
- 70 °C
Procedure
In accordance with the method described in Chemical and Pharmaceutical Bulletin, Vol. 16, No. 7, pages 1300 to 1307 (1968), 10 g of 2-hydroxycycloheptimidazole, 150 g of phosphorus oxychloride and 12 g of N,N-diethylaniline were stirred under heating at an internal temperature of 70° C. for 6 hours and 30 minutes. After the reaction, the phosphorus oxychloride was evaporated off under reduced pressure, and the resulting reaction mixture was poured into 500 ml of ice-water. Sodium hydrogencarbonate was added to the resulting solution until the pH thereof became neutral, and this was extracted with chloroform (250 ml×2). The chloroform layer was dried with anhydrous sodium sulfate and the solvent was evaporated off, and then the reaction product was purified by silica gel column chromatography with a developer solvent of ethyl acetate. 2.7 g of colorless crystals were obtained.
Workup
- customAfter the reaction
- customthe phosphorus oxychloride was evaporated off under reduced pressure
- customthe resulting reaction mixture
- extractionthis was extracted with chloroform (250 ml×2)
- dry with materialThe chloroform layer was dried with anhydrous sodium sulfate
- customthe solvent was evaporated off
- customthe reaction product was purified by silica gel column chromatography with a developer solvent of ethyl acetate
Sources & evidence
- ORD record
- ord-aaf86bab097f4cf7b5ef5da2668dab90
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05003077
Reaction notes
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