Hydrogen Bromide → N-[4-[4-(ethylheptylamino)butyl]phenyl]methanesulfonamide monohydrobromide
Reaction equation
[CH2:1]([N:3]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=1)[CH3:2].[BrH:26]>C(OCC)C>[BrH:26].[CH2:1]([N:3]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:12][CH:13]=1)[CH3:2]Participants
4
Procedure
N-[4-[4-(ethylheptylamino)butyl]phenyl]methanesulfonamide (5.56 g, 0.015 mol), prepared according to the general procedure outlined in Example 1, was dissolved in diethyl ether. The solution was cooled with a dry ice/acetone bath and diethyl ether saturated with hydrogen bromide gas was added thereto. The volatiles were evaporated under reduced pressure and 100 ml of ethyl acetate was added to the residue. The solution was triturated and approximately 6 grams of crystals were collected. The solid was recrystalized from isopropyl alcohol to provide 2.5 g of N-[4-[4-(ethylheptylamino)butyl]phenyl]methanesulfonamide monohydrobromide. mp=98°-100° C. Yield 37%
Workup
- temperatureThe solution was cooled with a dry ice/acetone bath
- customThe volatiles were evaporated under reduced pressure and 100 ml of ethyl acetate
- additionwas added to the residue
- customThe solution was triturated
- customapproximately 6 grams of crystals were collected
- customThe solid was recrystalized from isopropyl alcohol
Sources & evidence
- ORD record
- ord-70253ae8ff4f441392973bf47651d6ac
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04596827
Reaction notes
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