4,4'-Diethylbenzophenone → Ethyl 4-[3,3-bis-(p-tolyl)propionamido]benzoate
Reaction equation
C(OP(CC(NC1C=CC(C(OCC)=O)=CC=1)=O)(OCC)=O)C.C(C1C=CC(C(C2C=CC(CC)=CC=2)=O)=CC=1)C.[C:42]1([CH3:71])[CH:47]=[CH:46][C:45]([C:48]([C:64]2[CH:69]=[CH:68][C:67]([CH3:70])=[CH:66][CH:65]=2)=[CH:49][C:50]([NH:52][C:53]2[CH:63]=[CH:62][C:56]([C:57]([O:59][CH2:60][CH3:61])=[O:58])=[CH:55][CH:54]=2)=[O:51])=[CH:44][CH:43]=1>>[C:42]1([CH3:71])[CH:43]=[CH:44][C:45]([CH:48]([C:64]2[CH:65]=[CH:66][C:67]([CH3:70])=[CH:68][CH:69]=2)[CH2:49][C:50]([NH:52][C:53]2[CH:63]=[CH:62][C:56]([C:57]([O:59][CH2:60][CH3:61])=[O:58])=[CH:55][CH:54]=2)=[O:51])=[CH:46][CH:47]=1Participants
Procedure
Certain of the compounds of this invention are prepared directly by the reaction of substituted diethyl phosphonoacetanilides with benzophenones. The requisite substituted diethyl phonsphonoacetanilides are prepared as follows. Treatment of bromoacetyl bromide with a substituted aniline yields a substituted bromoacetanilide. Reaction of the bromoacetanilide with triethylphosphite affords the substituted diethyl phosphonoacetanilide required for reaction with a benzophone. An example of this series of reactions is the acylation of ethyl 4-aminobenzoate to yield ethyl 4-bromoacet anilide followed by reaction with triethyl phosphite to yield ethyl 4-[(diethylphosphono)acetamido]benzoate. Reaction of this diethylphosphonoacetanilide with 4,4'-diethylbenzophenone then affords ethyl 4-[3,3-bis-(p-tolyl)acrylamido]benzoate directly. If the saturated analog is desired, catalytic hydrogenation of this ester may be used to obtain ethyl 4-[3,3-bis-(p-tolyl)propionamido]benzoate.
Sources & evidence
- ORD record
- ord-06ac7febf697470f80400742da9787d9
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04536346
Reaction notes
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