Cesium carbonate → HCID 68430453, compound

HRID 2244019Notes

Reaction equation

HRID 2244019 reaction equation
Cl[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1.[OH:20][C:21]1[C:26]([CH2:27][CH2:28][CH3:29])=[C:25]([OH:30])[CH:24]=[CH:23][C:22]=1[C:31](=[O:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:31]([C:22]1[CH:23]=[CH:24][C:25]([O:30][CH2:2][C:3]2[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)=[O:8])=[CH:5][CH:4]=2)=[C:26]([CH2:27][CH2:28][CH3:29])[C:21]=1[OH:20])(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 43333337HCID 43333337, compound

Product 1

HCID 68430453HCID 68430453, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 4-chloromethyl-N-(4-cyano-phenyl)-benzamide (1.00 g, 3.69 mmol) to a solution of 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (717 mg, 3.69 mmol) in dimethylformamide (14 mL). After 10 minutes add potassium carbonate (766 mg, 5.54 mmol) and cesium carbonate (1.204 g, 3.69 mmol). Stir at room temperature for one hour, then heat to 70° C. for 1.5 hours. Cool, and partition between ethyl acetate (100 mL) and water (100 mL). The organic phase is washed twice with water, brine, dried, and concentrated to dryness. The resulting residue is purified by silica gel column chromatography, eluting with 1:1 hexane:ethyl acetate to afford the title compound (820 mg, 52%): 1H NMR (CDCl3) δ 0.97 (t, 3H), 1.58 (m, 2H), 2.56 (s, 3H), 2.73 (m, 2H), 5.25 (s, 2H), 6.46 (d, 1H), 7.56-7.60 (m, 3H), 7.68 (d, 2H), 7.79 (d, 2H), 7.88-7.94 (m, 3H), 12.77 (s, 1H).

Workup

  1. temperatureheat to 70° C. for 1.5 hours
  2. temperatureCool
  3. custompartition between ethyl acetate (100 mL) and water (100 mL)
  4. washThe organic phase is washed twice with water, brine
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe resulting residue is purified by silica gel column chromatography
  8. washeluting with 1:1 hexane

Sources & evidence

ORD record
ord-4c6e68ee6d2643c2972251a805417ee1
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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