Dimethylformamide → HCID 353402, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[C:11](=[O:14])([O-])[O-:12].[K+].[K+].[C:17]([CH2:20][CH2:21]Br)(=[O:19])[CH3:18].[CH3:23]N(C=O)C>>[C:11]([O:12][CH2:17][CH2:18][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])(=[O:14])[CH3:23].[C:17]([CH2:20][CH2:21][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])(=[O:19])[CH3:18]Participants
Procedure
3.0 g (21.9 mmol) of the 3-hydroxybenzamide prepared in Example 1 and 5.7 g (41.2 mmol) of anhydrous potassium carbonate were added to a round bottom flask followed by 40 ml anhydrous DMF added by syringe. To this mixture was added 11.85 g (70.9 mmol, 7.8 cc) of 2-acetoyl ethyl bromide, also using a syringe to maintain anhydrous conditions. The suspension was stirred for 48 hr and the mixture filtered. The solid was washed with 6×5 ml DMF and the filtrate evaporated in vacuo to a solid. The resulting solid was recrystallized from 90% aqueous alcohol and the solid from the filtration was washed with cold 90% alcohol and ether. The desired product, 3-(2-acetoylethoxy)benzamide was obtained in 65% yield (3.2 g), mp 121°-122° C. Identity of the product was confirmed by TLC and by elemental analysis. Calculated for C11H13NO4 ; C: 59.18; H: 5.87; N: 6.28; Found: C: 59.03; H: 5.83; N: 6.58.
Workup
- additionadded by syringe
- temperatureto maintain anhydrous conditions
- filtrationthe mixture filtered
- washThe solid was washed with 6×5 ml DMF
- customthe filtrate evaporated in vacuo to a solid
- customThe resulting solid was recrystallized from 90% aqueous alcohol
- filtrationthe solid from the filtration
- washwas washed with cold 90% alcohol and ether
Sources & evidence
- ORD record
- ord-935808a55471453dba3e9cc5c8c67519
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05041653
Reaction notes
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