Lawesson's reagent → HCID 59829893, compound

HRID 1947193Notes

Reaction equation

HRID 1947193 reaction equation
[CH2:1]([O:8][C:9]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:27]([CH:38]([CH3:40])[CH3:39])=[CH:26][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:50])=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:27]([CH:38]([CH3:40])[CH3:39])=[CH:26][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=[S:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 59829891HCID 59829891, compound

Product 1

HCID 59829893HCID 59829893, compoundYield 161.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

2,4-bis-benzyloxy-5-isopropyl-N-[4-(morpholin-4-yl)phenyl]benzamide (F370-IM2, 2.45 g, 4.60 mmol) was suspended in toluene (50 mL), mixed with Lawesson's reagent (2.05 g, 5.06 mmol) and the mixture was heated at 110° C. for 1 hour. As the reaction proceeded, the suspension changed to a yellow solution. The reaction mixture was cooled to room temperature, mixed with 5% aqueous sodium hydrogencarbonate (50 mL), and the organic layer was separated. The organic layer thus obtained was dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and the solvent was distilled off under reduced pressure. To the residue were added toluene (20 mL) and hexane (10 mL), and the resulting suspension was stirred at room temperature for 1 hour, crystals (F370-IM3) were collected by filtration. The mother liquor was concentrated and purified by silica gel column chromatography (ethyl acetate:hexane 2:1), to afford F370-IM3. The combined title compound (F370-IM3, about 4.1 g) was subjected to the next reaction.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the residue were added toluene (20 mL) and hexane (10 mL)
  8. filtrationcrystals (F370-IM3) were collected by filtration
  9. concentrationThe mother liquor was concentrated
  10. custompurified by silica gel column chromatography (ethyl acetate:hexane 2:1)
  11. customto afford F370-IM3

Sources & evidence

ORD record
ord-b341a4bf3d2247bc810b941130f3c13e
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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