Reaction equation
[CH:1]1[C:11]2[C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19].C(O)C.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[N:25]1([CH2:19][CH2:18][C:17]([N:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]2=3)=[O:20])[CH2:29][CH2:28][CH2:27][CH2:26]1Participants
6
Procedure
6.3 gm (0.03 mol) of 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and 3.3 gm (0.036 mol) of acrylic acid chloride were refluxed, while stirring, in 200 ml of toluene for 3 hours. The reaction mixture was then evaporated in vacuo. The dry residue was admixed with 200 ml of ethanol, and 2.5 gm (0.035 mol) of pyrrolidine were added dropwise, while stirring, to the boiling solution. Subsequently, the reaction mixture was heated for 20 minutes, then evaporated in vacuo to about 1/10 of its original volume, and discolored by filtration through activated charcoal/silica gel. The crude product was recrystallized from a little ethyl acetate.
Workup
- customThe reaction mixture was then evaporated in vacuo
- additionwere added dropwise
- temperatureSubsequently, the reaction mixture was heated for 20 minutes
- customevaporated in vacuo to about 1/10 of its original volume
- filtrationdiscolored by filtration through activated charcoal/silica gel
- customThe crude product was recrystallized from a little ethyl acetate
Sources & evidence
- ORD record
- ord-993854165d8f4ec4a76a748cfa519fad
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04377576
Linked notes
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