Potassium Carbonate → HCID 86689286, compound

HRID 537303Notes

Reaction equation

HRID 537303 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][C:3]=1[NH:11][CH2:12][CH:13]([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+].[Cl:22][C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29](Cl)=[O:30])=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+]>CC#N.CCOC(C)=O>[Cl:22][C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][C:3]=2[NH:11][CH2:12][CH:13]([CH3:14])[CH3:15])=[O:30])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 77771p-Chlorophenoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 86689287HCID 86689287, compound

Product 1

HCID 86689286HCID 86689286, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 55 (2.08 g, 0.01 mol) and K2CO3 (3.45 g, 0.025 mol) in CH3CN (25 mL) was added a solution of 56a (2.46 g, 0.012 mol) in CH3CN (25 mL) over 45 min at rt under Ar. After stirring at rt for 3 hr, EtOAc (100 mL) and saturated NaHCO3 (100 mL) where added. The resulting mixture was stirred at rt for 10 min. The organic phase was washed with saturated NaHCO3 (1×75 mL) and brine (1×100 mL), filtered through phase separation filter paper, and concentrated in vacuo to give a solid. The solid was triturated with hexanes (100 mL), filtered, and dried to give 3.5 g (93%) of 58a as a purple solid. HPLC analysis showed a purity of 91%. 1H NMR (60 MHz, CDCl3): δ 7.6 (brs, 1H), 7.3-6.7 (m, 5H), 6.2 (m, 2H), 4.6 (s, 2H), 4.0 (q, 2H), 3.6 (brs, 1H), 2.8 (brs, 2H), 2.0-1.6 (m, 1H), 1.4 (t, 3H), 1.0 (d, 6H) ppm.

Workup

  1. stirringThe resulting mixture was stirred at rt for 10 min
  2. washThe organic phase was washed with saturated NaHCO3 (1×75 mL) and brine (1×100 mL)
  3. filtrationfiltered through phase separation
  4. filtrationfilter paper
  5. concentrationconcentrated in vacuo
  6. customto give a solid
  7. customThe solid was triturated with hexanes (100 mL)
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-08c3b26d712f4bc896e6418a1ec92bd1
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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