Hydrochloric Acid → 2-[(4-Bromophenyl)thio]-N,N-dimethylethanamine
Reaction equation
Cl[CH2:2][CH2:3][N:4]([CH3:6])[CH3:5].Cl.[OH-].[Na+].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1>C(O)C>[CH3:5][N:4]([CH2:3][CH2:2][S:17][C:14]1[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][CH:13]=1)[CH3:6]Participants
Procedure
A solution of 23.5 g of chloroethyldimethylamine.HCl in 75 ml of ethanol was added to 160 ml of sodium hydroxide solution formed by dissolving 20 g of sodium hydroxide pastilles in 500 ml of ethanol. A solution of 30 g of 4-bromothiophenol in 100 ml of ethanol was added to 160 ml of the said sodium hydroxide solution and the first solution was added thereto over 2 minutes at 20° C. The mixture was refluxed for 3 hours and was evaporated to dryness. Water was added to the residue and the mixture was extracted with methylene chloride. The organic phase was washed with aqueous 0.1 N sodium hydroxide solution, then with water, dried and evaporated to dryness. The residue was distilled to obtain 35.5 g of 4-(N,N-dimethylaminoethylthio)-bromobenzene boiling at 110° C. at 0.1 mm Hg.
Workup
- customformed
- additionthe first solution was added
- temperatureThe mixture was refluxed for 3 hours
- customwas evaporated to dryness
- additionWater was added to the residue
- extractionthe mixture was extracted with methylene chloride
- washThe organic phase was washed with aqueous 0.1 N sodium hydroxide solution
- dry with materialwith water, dried
- customevaporated to dryness
- distillationThe residue was distilled
Sources & evidence
- ORD record
- ord-90e9ceabe8734a3fbcc74f764d7963a6
- Source dataset
- uspto-grants-1984_05
- Patent number
- US04447424
Reaction notes
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