Sodium ethoxide → HCID 19699312, compound

HRID 863088Notes

Reaction equation

HRID 863088 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[C:15](CN(C)C)=[C:14](CN(C)C)[N:13]=[C:12]1[S:24]CCC(OCC)=O.[O-]CC.[Na+].[Na]>C(O)C>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[C:15]([N:11]([CH3:15])[CH3:2])=[C:14]([N:13]([CH3:14])[CH3:12])[NH:13][C:12]1=[S:24]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 19699398HCID 19699398, compound

Product 1

HCID 19699312HCID 19699312, compoundYield 116.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of ethyl 3-[1-(1,2,3,4-tetrahydronaphthalen-2-yl)-4,5-di(dimethylaminomethyl)imidazol-2-ylthio]propionate (0.55 g, 1.2 mmol) and sodium ethoxide (3.5 mL of a solution prepared free 450 mg sodium in 45 mL of ethanol, 1.4 mmol) in 5 mL of ethanol was stirred at approximately 25° C. for 1.75 hours. The mixture was concentrated and partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried (K2CO3), filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (97:3) to give 1-(1,2,3,4-tetrahydronaphthalen-2-yl)-4,5-di(dimethylamino)-1,3-dihydroimidazole-2-thione (0.24 g, 0.7 mmol), m.p. 182°-184° C.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (K2CO3)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (97:3)

Sources & evidence

ORD record
ord-c6601beadd8a4dfa944af6b0dab3e8b6
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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