Lawesson's reagent → HCID 58875330, compound

HRID 2079988Notes

Reaction equation

HRID 2079988 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=O)=[CH:11][CH:10]=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:38]2)=CC=1>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=[S:38])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58387946HCID 58387946, compound

Product 1

HCID 58875330HCID 58875330, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the resulting quinoline-6-carboxylic acid 4-benzyloxy-benzylamide (310 mg, 0.84 mmol), 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (Lawesson's reagent) (1.4 g, 3.4 mmol) and tetrahydrofuran (10 mL) was refluxed for 1 hour. After cooling, the solvent was evaporated in vacuo, dichloromethane was added to the residue, which was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (55 mg, 0.14 mmol, 17%) was obtained as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe solvent was evaporated in vacuo, dichloromethane
  4. additionwas added to the residue, which
  5. customwas purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-21a4db59af0b4d3db0df597a27641016
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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