Potassium Carbonate → HCID 68871299, compound

HRID 2112039Notes

Reaction equation

HRID 2112039 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][S:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])[CH:5]=[CH:6][CH:7]=1.[CH2:21]([N:28]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:29](=[O:32])[CH2:30]Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:21]([N:28]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:29](=[O:32])[CH2:30][O:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][S:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])[CH:5]=[CH:6][CH:7]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68872277HCID 68872277, compoundHCID 68873442Methyl 2-([2-(3-hydroxyphenyl)ethyl]thio}benzoate

Product 1

HCID 68871299HCID 68871299, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-{[2-(3-hydroxyphenyl)ethyl]thio}benzoate (129 mg, 0.447 mmol), N-benzyl-2-bromo-N-hexylacetamide (154 mg, 0.492 mmol) and potassium carbonate, anhydrous (93 mg, 0.671 mmol) were mixed in acetonitrile (10 ml). The mixture was heated to reflux overnight and then evaporated to dryness. Water and ethyl acetate were added into the residue. The two phases were separated. The organic phase was washed with brine and dried with magnesium sulphate and then evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using ethyl acetate/heptane (10:90, then 25:75) as eluant gave 208 mg the desired product, yield 89.5%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated to dryness
  4. additionWater and ethyl acetate were added into the residue
  5. customThe two phases were separated
  6. washThe organic phase was washed with brine
  7. dry with materialdried with magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-9acd7911ef94466eb2786651b1712e0c
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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