HCID 21432236, compound → HCID 21432233, compound

HRID 2399002Notes

Reaction equation

HRID 2399002 reaction equation
C[N:2](C)C1SC(C2N(C)C([N+]([O-])=O)=CN=2)=NN=1.CNC1SC(C2N(C)C([N+]([O-])=O)=CN=2)=NN=1.[NH2:34][C:35]1[S:36][C:37]([C:40]2[N:41]([CH2:48][CH2:49]O)[C:42]([N+:45]([O-:47])=[O:46])=[CH:43][N:44]=2)=[N:38][N:39]=1>>[NH2:34][C:35]1[S:36][C:37]([C:40]2[N:41]([CH2:48][CH3:49])[C:42]([N+:45]([O-:47])=[O:46])=[CH:43][N:44]=2)=[N:38][N:39]=1.[CH2:48]([N:41]1[C:42]([N+:45]([O-:47])=[O:46])=[CH:43][N:44]=[C:40]1[C:37]([NH:38][NH:39][C:35]([NH2:34])=[S:36])=[NH:2])[CH3:49]

Participants

5

Reactant 3

HCID 21432236HCID 21432236, compoundHCID 21432257HCID 21432257, compoundHCID 21432273HCID 21432273, compound

Product 2

HCID 21432233HCID 21432233, compoundHCID 178462844HCID 178462844, compound

Procedure

In a similar manner, 4,4-dimethyl-1-(1-methyl-5-nitro-2-imidazolecarboximidoyl)-3-thiosemicarbazide, 4-methyl-1-(1-methyl-5-nitro-2-imidazolecarboximidoyl)-3-thiosemicarbazide and 1-(1-[2-hydroxyethyl]-5-nitro-2-imidazolecarboximidoyl)-3-thiosemicarbazide yield respectively, 2-(2-dimethylamino-1,3,4-thiadiazol-5-yl)-1-methyl-5-nitroimidazole (VIIIE), 2-(2-methylamino-1,3,4-thiadiazol-5-yl)-1-methyl-5-nitroimidazole (VIIIC) and 2-(2-amino-1,3,4-thiadiazol-5-yl)-1-(2-hydroxyethyl)-5-nitroimidazole (VIIID). According to the above procedure, 2-(2-amino-1,3,4-thiadiazol-5-yl)-1-ethyl-5-nitroimidazole (VIIIE) is obtained from 1-(1-ethyl-5-nitro-2-imidazolecarboximidoyl)-3-thiosemicarbazide.

Sources & evidence

ORD record
ord-4139b34541284db197621dc4f985cce1
Source dataset
uspto-grants-1977_05
Patent number
US04026903

Reaction notes

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