Lawesson's reagent → HCID 11999036, compound

HRID 1364105Notes

Reaction equation

HRID 1364105 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=O)[CH2:3]1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:28]2)=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[S:28])[CH2:3]1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 6222625,5-DiMethyl-2-(Morpholin-4-yl)-5,6-dihydro-1,3-benzothiazol-7(4H)-one

Product 1

HCID 11999036HCID 11999036, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 48 (0.266 g, 1 mmol) in THF (10 mL) at r.t. was added 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (0.808 g, 2 mmol). The reaction mixture was stirred for 2 h and then poured into saturated NaHCO3 solution (50 ml) and extracted with DCM (2×50 mL). The combined organic fractions were dried over MgSO4, filtered and the solvent removed by evaporation in vacuo to give the title compound (0.14 g, 50%) as a solid. δH (DMSO-d6) 3.72-3.60 (8H, m), 2.74 (2H, s), 2.61 (2H, s), 1.02 (6H, s). LCMS (ES+) 283.0 (M+H)+.

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialThe combined organic fractions were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed by evaporation in vacuo

Sources & evidence

ORD record
ord-89308257ab8f478da89da0933b3d4b98
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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