Diethylamine → HCID 515394, compound
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19](=[O:22])[CH2:20]Br)=[CH:12][CH:13]=3)[C:8](=[O:23])[C:7]=2[CH:6]=1)=[O:4].[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25]>O1CCCC1>[CH2:24]([N:26]([CH2:27][CH3:28])[CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19](=[O:22])[CH2:20][N:26]([CH2:27][CH3:28])[CH2:24][CH3:25])=[CH:12][CH:13]=3)[C:8](=[O:23])[C:7]=2[CH:6]=1)=[O:4])[CH3:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
To a mixture of 2,7-bis(2-bromoacetyl)xanthen-9-one in tetrahydrofuran is added diethylamine, each cooled to -20°C. The reaction mixture is maintained at -20°C. for 24 hours then allowed to warm slowly to room temperature and then maintained at room temperature for 5 days. The mixture is filtered, and the filtrate evaporated to dryness. The resulting residue is dissolved in dilute HCl, filtered and the filtrate is made alkaline, keeping the temperature of the mixture around 0°C. The mixture is extracted with methylene chloride, and the extract acidified to Congo Red. The resulting solid is filtered off and recrystallized from methanol-diethylether to give the desired product.
Workup
- temperatureThe reaction mixture is maintained at -20°C. for 24 hours
- temperatureto warm slowly to room temperature
- temperaturemaintained at room temperature for 5 days
- filtrationThe mixture is filtered
- customthe filtrate evaporated to dryness
- dissolutionThe resulting residue is dissolved in dilute HCl
- filtrationfiltered
- customthe temperature of the mixture around 0°C
- extractionThe mixture is extracted with methylene chloride
- filtrationThe resulting solid is filtered off
- customrecrystallized from methanol-diethylether
Sources & evidence
- ORD record
- ord-7677e923fe4949cb927b98ac6df0e0f9
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03957989
Reaction notes
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