Lawesson's reagent → HCID 18623790, compound

HRID 1860451Notes

Reaction equation

HRID 1860451 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][O:15][C:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:17])[CH2:9]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][O:15][C:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:17])[CH2:9]1)=[S:39]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 16074372HCID 16074372, compound

Product 1

HCID 18623790HCID 18623790, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.7 g (3.66 mmol) of 4-(3′,4′,5′-trimethoxybenzoyl)-2-(N,N-diethylaminocarbonyloxymethyl)piperazine, prepared according to the protocol described in step 8.1 of Example 8, are dissolved in 34 ml of THF and cooled in an ice bath. 1.7 g (1 equivalent) of Lawesson's reagent are added portionwise thereto. The solution is stirred at 0° C. for 30 minutes and then at room temperature overnight. The solvent is then removed under vacuum and the residue is rapidly purified on a column of silica gel (eluents: CH2Cl2 and then 1% MeOH in CH2Cl2) to give 1.1 g of 4-(3′,4′,5′-trimethoxythiobenzoyl)-2-(N,N-diethylaminocarbonyloxymethyl)piperazine in the form of a viscous yellow product. Yield: 62.4%.

Workup

  1. temperaturecooled in an ice bath
  2. customat room temperature
  3. customovernight
  4. customThe solvent is then removed under vacuum
  5. customthe residue is rapidly purified on a column of silica gel (eluents

Sources & evidence

ORD record
ord-a563fc6a8c17456d8511b62d6ad94591
Source dataset
uspto-grants-2003_03
Patent number
US06531476B1

Reaction notes

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