Lawesson's reagent → HCID 19843389, compound

HRID 2352553Notes

Reaction equation

HRID 2352553 reaction equation
[CH2:1]([N:4]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:5]([C:7]1[S:11][CH:10]=[N:9][CH:8]=1)=O)[CH2:2][CH3:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>O>[CH2:1]([N:4]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:5]([C:7]1[S:11][CH:10]=[N:9][CH:8]=1)=[S:31])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19843394HCID 19843394, compound

Product 1

HCID 19843389HCID 19843389, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the N-propyl-N-[2-(4-chlorophenoxy)ethyl]thiazole-5-carboxamide (0.9 g, 3 mmol) obtained in Example 2B and Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide, 1.2g, 3 mmol) was refluxed for 20 hours and then cooled to room temperature. Water (100 ml) was added and the residue was extracted into ether (2×200 ml). The combined organic extract was washed with saturated sodium chloride solution (50 ml) and dried over magnesium sulphate. Evaporation of the solvent left an oil which, after flash chromatography on silica gel using 1:1 ethyl acetate: petroleum ether as the eluant, yielded the desired product as a yellow oil (0.75 g), M+ found: 340

Workup

  1. temperaturewas refluxed for 20 hours
  2. extractionthe residue was extracted into ether (2×200 ml)
  3. extractionThe combined organic extract
  4. washwas washed with saturated sodium chloride solution (50 ml)
  5. dry with materialdried over magnesium sulphate
  6. customEvaporation of the solvent
  7. waitleft an oil which

Sources & evidence

ORD record
ord-55c9452930bc469eb036157226219344
Source dataset
uspto-grants-1989_10
Patent number
US04877802

Reaction notes

Loading…