Ethanol → HCID 15950087, compound

HRID 2220457Notes

Reaction equation

HRID 2220457 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) δ 0.9 (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-0361713d6b7e406c8c9d5f6a2f9539d6
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

Loading…