Lawesson's reagent → HCID 19700826, compound

HRID 861975Notes

Reaction equation

HRID 861975 reaction equation
[CH2:1]([N:8]1[C:13](=O)[C:12]2[CH:15]=[CH:16][CH:17]=[N:18][C:11]=2[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:35]2)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:13](=[S:35])[C:12]2[CH:15]=[CH:16][CH:17]=[N:18][C:11]=2[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19700679HCID 19700679, compound

Product 1

HCID 19700826HCID 19700826, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-benzyl-8-(3-chlorophenyl)pyrido-[2,3-d]pyridazin-5-one (0.96 g, 2.76 mmoles) in toluene (100 mL) at room temperature under a nitrogen atmosphere was added solid 2,4-bis(4-methoxyphenyl)-l,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's Reagent) (0.67 g, 1.66 mmoles). The reaction mixture was heated under reflux for 18 hours, and then cooled and concentrated. Chromatography on silica gel using ethyl acetate/hexane (1:4) gave 0.233 g of 6-benzyl-8-(3-chlorophenyl)pyrido[2,3-d]pyridazin-5-thione (23.2%), mp 132° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperaturecooled
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8737c617b10545a880eba7f7ce21acdc
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

Loading…