Hydrogen Bromide → 4-(6-bromohexyloxy)-N-(2-hydroxyethyl)benzamide
Reaction equation
[OH:1][CH2:2][CH2:3][NH2:4].[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.Br>CN(C)C=O.C1(C)C=CC=CC=1.O>[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:4][CH2:3][CH2:2][OH:1])=[O:18])=[CH:15][CH:14]=1Participants
7
Procedure
To a stirred solution of 300 ml of 2-hydroxyethylamine in 1.2 liter of dimethylformamide at 0° C. was added dropwise 450 ml of 4-(6-bromohexyloxy)benzoyl chloride in 50 ml of toluene over a 30 minute period. After an additional 30 minutes of stirring, 48% hydrobromic acid (about 200 ml) was added until the pH reached 5-5.5, and the mixture was diluted with 1200 ml of water and extracted with isopropyl acetate (total of 2500 ml). The extracts were washed with water and saturated sodium chloride solution, filtered, and concentrated to a volume of about 1 liter. The mixture was cooled and the solid which separated was collected by filtration and dried at 40° C. to give 332.7 g of 4-(6-bromohexyloxy)-N-(2-hydroxyethyl)benzamide.
Workup
- extractionextracted with isopropyl acetate (total of 2500 ml)
- washThe extracts were washed with water and saturated sodium chloride solution
- filtrationfiltered
- concentrationconcentrated to a volume of about 1 liter
- temperatureThe mixture was cooled
- customthe solid which separated
- filtrationwas collected by filtration
- customdried at 40° C.
Sources & evidence
- ORD record
- ord-5aa3dced278e4759b120ea8c5578990f
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05002960
Reaction notes
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