Ammonium Chloride → 2-bromo-N-(2,4,6-trimethoxyphenyl)decanamide
Reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=O.[CH3:14][O:15][C:16]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[C:17]=1[NH2:18].[Cl-].[NH4+]>S(Cl)(Cl)=O.N1C=CC=CC=1>[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([NH:18][C:17]1[C:19]([O:25][CH3:26])=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:16]=1[O:15][CH3:14])=[O:5]Participants
6
Procedure
2-Bromodecanoic acid (1 g, 3.8 mmol) was heated under reflux in thionyl chloride (10 ml) for 1 hour. The thionyl chloride was evaporated and the residue was dissolved in dry ether (10 ml) and added dropwise to a solution of 2,4,6-trimethoxyaniline (0.7 g, 3.8 mmol) in pyridine (20 ml) at 0° C. and the mixture was stirred for 1.5 hours. The reaction mixture was poured into saturated aqueous ammonium chloride and extracted three times with ethyl acetate (60 ml). The combined organics were extracted with water and brine and dried and concentrated. Recrystallization from isopropyl ether afforded 1.1 g (65%) of the title compound, m.p. 109°-110° C. This material was used directly in the next step.
Workup
- customThe thionyl chloride was evaporated
- dissolutionthe residue was dissolved in dry ether (10 ml)
- extractionextracted three times with ethyl acetate (60 ml)
- extractionThe combined organics were extracted with water and brine
- customdried
- concentrationconcentrated
- customRecrystallization from isopropyl ether
Sources & evidence
- ORD record
- ord-a039717299314874b89da6ba08f56f92
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05362878
Reaction notes
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