Lawesson's reagent → HCID 86646757, compound

HRID 888377Notes

Reaction equation

HRID 888377 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)[CH:17]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:34]2)=CC=1.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)[CH:17]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[S:34]

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 68494793HCID 68494793, compound

Product 1

HCID 86646757HCID 86646757, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 3-[(methylamino)carbonyl]-5-(5-methylpyridin-2-yl)benzoate (1.0 g, 3.06 mmol) in dichloroethane (8 mL) was added 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (0.68 g, 1.69 mmol). The reaction mixture was heated to 50° C. After 3 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol) gave the title compound. MS 343.0 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol)

Sources & evidence

ORD record
ord-428cbdd352f64f8f89f63c0d4e394d57
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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