Pyridine → HCID 131715088, compound

HRID 1906734Notes

Reaction equation

HRID 1906734 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][S:17][C:18](SC)=[N:19]C#N.[N:24]1C=CC=C[CH:25]=1>>[C:25]([N:1]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)[C:18](=[NH:19])[S:17][CH3:16])#[N:24]

Participants

4

Reactant 3

HCID 1049PyridineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 161928Ici 109,081

Product 1

HCID 131715088HCID 131715088, compound

Procedure

(-)-6-(4-Aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (0.240 g) was stirred with dimethyl cyanodithioiminocarbonate (0.38 g) in dry pyridine (4 ml) under reflux for 6 hours. The reaction mixture was then evaporated down to an oily solid under vacuum at 50° C. Diethyl ether (approx. 20 ml) was added to the reaction mixture and stirred until a solid was obtained. The solid was then filtered and thoroughly washed with diethyl ether (approx. 20 ml) to give the corresponding 6-(4-(N-cyano-S-methylisothioureido)phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone.

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe reaction mixture was then evaporated down to an oily solid under vacuum at 50° C
  3. additionDiethyl ether (approx. 20 ml) was added to the reaction mixture
  4. customwas obtained
  5. filtrationThe solid was then filtered
  6. washthoroughly washed with diethyl ether (approx. 20 ml)

Sources & evidence

ORD record
ord-be65a897535641fbae6ba4941b064384
Source dataset
uspto-grants-1987_03
Patent number
US04654342

Reaction notes

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