3'-Aminoacetophenone → N,N'-bis(3-acetylphenyl)pentanediamide

HRID 1460067Notes

Reaction equation

HRID 1460067 reaction equation
C([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)[NH2:7])(=O)C.C(C1C=C(N[C:27](=O)[CH2:28][CH2:29][C:30]([NH:32][C:33]2[CH:38]=[C:37]([C:39](=[O:41])[CH3:40])[CH:36]=[C:35](C(=O)C)[CH:34]=2)=[O:31])C=C(C(=O)C)C=1)(=O)C.[C:46](C1C=C(NC(=O)CCCCC(NC2C=C(C(=O)C)C=C(C(=O)C)C=2)=O)C=C(C(=O)C)C=1)(=[O:48])C.C(C1C=C(NC(=O)CCCCCC(NC2C=C(C(=O)C)C=C(C(=O)C)C=2)=O)C=C(C(=O)C)C=1)(=O)C.C(C1C=C(NC(=O)CCCCCCC(NC2C=C(C(=O)C)C=C(C(=O)C)C=2)=O)C=C(C(=O)C)C=1)(=O)C.C(C1C=C(NC(=O)CCCCCCCC(NC2C=C(C(=O)C)C=C(C(=O)C)C=2)=O)C=C(C(=O)C)C=1)(=O)C.C(C1C=C(NC(=O)CCCCCCCCC(NC2C=C(C(=O)C)C=C(C(=O)C)C=2)=O)C=C(C(=O)C)C=1)(=O)C.C(C1C=C(NC(=O)CCCCCCCCCCC(NC2C=C(C(=O)C)C=C(C(=O)C)C=2)=O)C=C(C(=O)C)C=1)(=O)C.CC(C1C=CC=C(N)C=1)=O.C(Cl)(=O)CCCC(Cl)=O>>[C:39]([C:37]1[CH:38]=[C:33]([NH:32][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C:46]([NH:7][C:6]2[CH:5]=[CH:4][CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[CH:8]=2)=[O:48])[CH:34]=[CH:35][CH:36]=1)(=[O:41])[CH3:40]

Participants

11

Reactant 10

HCID 74173'-AminoacetophenoneHCID 17887Pentanedioyl dichlorideHCID 463010Cni H1894HCID 15541276N,N'-bis(3,5-diacetylphenyl)butanediamideHCID 15541277HCID 15541277, compoundHCID 15541278HCID 15541278, compoundHCID 15541279HCID 15541279, compoundHCID 15541280N,N'-bis(3,5-diacetylphenyl)nonanediamideHCID 15541281N~1~,N~10~-Bis(3,5-diacetylphenyl)decanediamideHCID 15541282HCID 15541282, compound

Product 1

HCID 1010291N,N'-bis(3-acetylphenyl)pentanediamide

Procedure

Analogously, the following were prepared from 3,5-diacetylaniline and the corresponding dioyl dichlorides: N,N'-bis(3,5-diacetylphenyl)butanediamide, mp 293°-60° C.; N,N'-bis(3,5-diacetylphenyl)hexanediamide, mp 269°-70° C.; N,N'-bis(3,5-diacetylphenyl)heptanediamide, mp 200°-3° C.; N,N'-bis(3,5-diacetylphenyl)octanediamide, mp 183°-4° C.; N,N'-bis(3,5-diacetylphenyl)nonanediamide, mp 179°-80° C.; N,N'-bis(3,5-diacetylphenyl)decanediamide, mp 196°-9° C.; N,N'-bis(3,5-diacetylphenyl)dodecanediamide, mp 178°-9° C.; N,N'-bis(3,5-diacetylphenyl)(isophthalic acid diamide), mp 283°-4° C. Also analogously, N,N'-bis(3-acetylphenyl)pentanediamide, mp 174°-5° C. was prepared from 3-aminoacetophenone and glutaryl dichloride.

Sources & evidence

ORD record
ord-8fa306d6c59941ca9bf98e0001262fb9
Source dataset
uspto-grants-1998_12
Patent number
US05854289

Reaction notes

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