Ethanol → HCID 15950087, compound

HRID 646237Notes

Reaction equation

HRID 646237 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([C:10](=O)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15]C=2)=O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:20]([OH:22])C.Cl.[CH3:24][NH:25][C:26]([NH2:28])=[NH:27].C([O-])([O-])=O.[K+].[K+]>O>[NH2:28][C:26]1[N:25]([CH3:24])[C:20](=[O:22])[C:10]([C:8]2[S:9][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:6][CH:7]=2)([C:11]2[CH:13]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:27]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 68702180HCID 68702180, compoundHCID 178485118HCID 178485118, compound

Product 1

HCID 15950087HCID 15950087, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(5-butyl-thiophen-2-yl)-2-phenyl-ethane-1,2-dione was dissolved in a solution containing ethanol (15 mL) and water (3 mL). Into this mixture was added 1-methylguanidine hydrochloride (0.32 g, 3 mmol), and followed by K2CO3 (1.2 g, 0.9 mmol). The reaction was set to reflux 3 h, and then cooled to room temperature and the ethanol removed under reduced pressure. The crude product was taken in water (50 mL) and extracted with CHCl3 (3×). The organic layers were separated and combined, then dried over MgSO4, filtered and stripped. The crude product was purified by flash chromatography on silica gel in 10% methanol/ethyl acetate. A white solid was obtained. MS m/e 328 (M)+; 1HNMR (DMSO-d6, 300 MHz) δ0.9 (m, 3H), 1.2 (m, 2H), 1.5 (m, 1H), 2.6 (t, 2H), 2.95 (s, 3H), 6.5 (s, 1H), 6.6 (b, 2H), 6.8 (s, 1H), 7.2 (m, 3H), 7.5 (m, 2H).

Workup

  1. temperatureto reflux 3 h
  2. customthe ethanol removed under reduced pressure
  3. extractionextracted with CHCl3 (3×)
  4. customThe organic layers were separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe crude product was purified by flash chromatography on silica gel in 10% methanol/ethyl acetate
  8. customA white solid was obtained

Sources & evidence

ORD record
ord-4428beec57cc4753a2c78ec6feac0c3e
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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