Water → HCID 11078069, compound
Reaction equation
[H-].[Na+].[CH:3]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Br[CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1.O>CN(C)C=O>[CH:13]1[C:14]2[N:15]([CH2:18][CH2:19][O:20][C:21]3[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=3)[C:16]3[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:8][C:9]=2[CH:10]=[CH:11][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a suspension of sodium hydride (60% mineral oil, 0.13 g, 3.24 mmol) in dimethyl formamide (3 ml) was added phenoxazine (0.5 g, 2.7 mmol) in dimethyl formamide (5 mL). The reaction mixture was stirred at 25° C. for 0.5 h and a solution of 4-(2-bromoethoxy)benzaldehyde (0.74 g, 3.24 mmol) in dimethyl formamide (3 mL) was added. The reaction mixture was stirred at 25° C. for 6 h. Water (25 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with water (50 ml), brine solution (50 ml) and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed over silica gel using a mixture of ethyl acetate and pet. ether (3:7) as eluent to afford the title compound (0.52 g, 57%) as a syrupy liquid.
Workup
- stirringThe reaction mixture was stirred at 25° C. for 6 h
- extractionthe mixture was extracted with ethyl acetate (2×50 ml)
- washThe combined organic layers were washed with water (50 ml), brine solution (50 ml)
- dry with materialdried (Na2SO4)
- customThe solvent was evaporated
- customthe residue was chromatographed over silica gel using
- additiona mixture of ethyl acetate and pet. ether (3:7) as eluent
Sources & evidence
- ORD record
- ord-7c3e361d640542719887cb75a450c645
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06011031
Reaction notes
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