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 0.1N 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 0.1N sodium hydroxide solution
- dry with materialwith water, dried
- customevaporated to dryness
- distillationThe residue was distilled
Sources & evidence
- ORD record
- ord-506df67d1d1c4b4598b83913ae05fe01
- Source dataset
- uspto-grants-1985_05
- Patent number
- US04519946
Reaction notes
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