Nitrobenzene → HCID 178479343, compound
Reaction equation
[Cl:1]C1(Cl)CC1C1C=CC(NC(NC#N)=N)=CC=1.Cl.Cl.NCCCCCCN.[N+](C1C=CC=CC=1)([O-])=O.[Cl:37][C:38]1([Cl:78])[CH2:40][CH:39]1[C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:48](=[NH:77])[NH:49][C:50](=[NH:76])[NH:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][NH:58][C:59]([NH:61][C:62]([NH:64][C:65]2[CH:70]=[CH:69][C:68]([CH:71]3[CH2:73][C:72]3([Cl:75])[Cl:74])=[CH:67][CH:66]=2)=[NH:63])=[NH:60])=[CH:43][CH:42]=1>>[ClH:1].[Cl:37][C:38]1([Cl:78])[CH2:40][CH:39]1[C:41]1[CH:42]=[CH:43][C:44]([NH:47][C:48](=[NH:77])[NH:49][C:50](=[NH:76])[NH:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][NH:58][C:59]([NH:61][C:62]([NH:64][C:65]2[CH:70]=[CH:69][C:68]([CH:71]3[CH2:73][C:72]3([Cl:75])[Cl:74])=[CH:67][CH:66]=2)=[NH:63])=[NH:60])=[CH:45][CH:46]=1Participants
5
Procedure
A mixture of 1-(p-(2,2-dichlorocyclopropyl)phenyl)- 3-cyanoguanidine (8.3 g.), hexamethylenediamine dihydrochloride (2.8 g.) and nitrobenzene (30 g.) was stirred and heated (at 140°-145° C.) for four hours, cooled and filtered. The filter cake was slurried in a mixture of acetone (75 g.) and acetic acid (7 g.), then hot ethanol (300 g.), affording a light tan solid (2.3 g.), whose thin layer chromatogram showed a substantial amount of 1,1'-hexamethylenebis(5-(p-(2,2-dichlorocyclopropyl)phenyl)biguanide) but also a substantial amount of impurity.
Workup
- temperatureheated (at 140°-145° C.) for four hours
- temperaturecooled
- filtrationfiltered
- additionThe filter cake was slurried in a mixture of acetone (75 g.) and acetic acid (7 g.)
- customhot ethanol (300 g.), affording a light tan solid (2.3 g.), whose thin layer chromatogram
Sources & evidence
- ORD record
- ord-427100dcc0b749018a92fec28d7304f5
- Source dataset
- uspto-grants-1977_10
- Patent number
- US04053636
Reaction notes
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