Lawesson's reagent → HCID 18715215, compound

HRID 1066321Notes

Reaction equation

HRID 1066321 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19]([C:22]([CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=O)[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:31]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:41]2)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19]([C:22]([CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)=[S:41])[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:31]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 15839765HCID 15839765, compound

Product 1

HCID 18715215HCID 18715215, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolve 0.50 g (0.12 m mole) of 8-chloro-11-[1-(1-(3-pyridyl)methylcarbonyl)-4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]-pyridine (Example 2 of Table 2) and 0.5 g (0.12 m mole) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's Reagent) in 15 mL of toluene and stirr for 18 hours at room temperature and 18 hours at 80° C., under nitrogen. Filter the reaction mixture and concentrate under vacuo. Disolve the residue in 50 mL of 1N HCl and extract with 200 mL of CH2Cl2. The water layer was neutralized with Na2CO3 and extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated under vacuo giving the product as a white solid, mp=92-93° C.

Workup

  1. custom18 hours
  2. customat 80° C.
  3. filtrationFilter the reaction mixture
  4. concentrationconcentrate under vacuo
  5. extractionextract with 200 mL of CH2Cl2
  6. extractionextracted with CH2Cl2
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-9b12919aaed544d8a6f356e98746aa96
Source dataset
uspto-grants-2001_06
Patent number
US06242458B1

Reaction notes

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