Sodium Carbonate → HCID 59829873, compound

HRID 1947202Notes

Reaction equation

HRID 1947202 reaction equation
[CH2:1]([O:4][C:5]1[CH:26]=[C:25]([O:27][CH2:28][CH:29]=[CH2:30])[C:24]([CH2:31][C:32]#[C:33][CH3:34])=[CH:23][C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:12][CH:11]=1)=O)[CH:2]=[CH2:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:26]=[C:25]([O:27][CH2:28][CH:29]=[CH2:30])[C:24]([CH2:31][C:32]#[C:33][CH3:34])=[CH:23][C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:12][CH:11]=1)=[S:44])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 87949Lawesson's reagentHCID 59829924HCID 59829924, compound

Product 1

HCID 59829873HCID 59829873, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,4-bis-allyloxy-5 (but-2-ynyl)-N-[4-(morpholin-4-ylmethyl)-phenyl]-benzamide (F470-IM09: 400 mg, 0.86 mmol) and Lawesson's reagent (352 mg, 0.86 mmol) were dissolved in toluene (20 mL), and the mixture was heated under reflux for 3 hours. The reaction mixture was mixed with saturated aqueous sodium carbonate (30 mL) and extracted twice with ethyl acetate (40 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (ethyl acetate) to obtain the crude title compound (F470-IM10:240 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted twice with ethyl acetate (40 mL)
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a2ea93d7600b429782e9f0ca5899c0cc
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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