Imidazole → HCID 20202114, compound

HRID 979286Notes

Reaction equation

HRID 979286 reaction equation
BrC1C=C(C=O)SC=1.N1C=CN=C1.N1(C2C=C(C=O)SC=2)C=CN=C1.[N:26]1([C:31]2[CH:32]=[C:33]([C:36](=O)[CH2:37][CH2:38][C:39]([OH:41])=O)[S:34][CH:35]=2)[CH:30]=[CH:29][N:28]=[CH:27]1.O.[NH2:44][NH2:45]>>[N:26]1([C:31]2[CH:32]=[C:33]([C:36]3[CH2:37][CH2:38][C:39](=[O:41])[NH:44][N:45]=3)[S:34][CH:35]=2)[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

6

Reactant 5

HCID 795ImidazoleHCID 24654Hydrazine hydrate (1:1)HCID 877924-Bromothiophene-2-carbaldehydeHCID 133187124-(1H-Imidazol-1-yl)thiophene-2-carbaldehydeHCID 20202129HCID 20202129, compound

Product 1

HCID 20202114HCID 20202114, compound

Procedure

4-Bromo-thiophen-2-aldehyde is reacted with imidazol to 4-(imidazol-1-yl)-thiophen-2-aldehyde which is reacted with the necessary acid nitrile to 4-[4-(imidazol-1-yl)-thien-2-yl]-4-oxo-butyric acid nitrile which is hydrolized to 4-[4-(imidazol-1-yl)-thien-2-yl]-4-oxo-butyric acid. This compound is reacted with hydrazine hydrate to yield 4.5-dihydro-6-[4-(imidazol-1-yl)-thien-2-yl]-3-(2H)-pyridazinone which is subsequently dehydrogenated with 3-nitrobenzolsulfonic acid.

Sources & evidence

ORD record
ord-8cbeea1a54574b039fce5a1f0c62037f
Source dataset
uspto-grants-1987_05
Patent number
US04667033

Reaction notes

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