Potassium Carbonate → HCID 18784785, compound

HRID 1108523Notes

Reaction equation

HRID 1108523 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.C1(C(C2C=CC=CC=2)=CC[N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]3=[O:32])[CH2:19][CH2:18]2)C=CC=CC=1.F[C:40]1[CH:47]=[CH:46][C:43]([CH:44]=[O:45])=[CH:42][CH:41]=1>CN(C)C(=O)C.C(Cl)Cl>[OH:45][CH:44]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:43]1[CH:46]=[CH:47][C:40]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]3=[O:32])[CH2:21][CH2:22]2)=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 131720603HCID 131720603, compound

Product 1

HCID 18784785HCID 18784785, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
125 °C

Procedure

Potassium carbonate (10.6 g, 76.5 mmol) was added to a solution of Example 2 Part A compound (15.0 g, 69.6 mmol) and 4-fluorobenzaldehyde (Aldrich) (8.61 g, 69.6 mmol) in N,N-dimethylacetamide (100 mL) and the reaction was stirred at 125° C. for 24 h, then cooled to RT. The reaction was dissolved in CH2Cl2 (500 mL) and washed with water (4×180 mL) and brine (2×200 mL), then dried over MgSO4. Evaporation gave a solid mass. The crude product was triturated with EtOAc (10 mL), then washed with EtOAc (10 mL) and filtered to give title compound (17.8 g, 80%) as a white solid (mp 211-214° C.).

Workup

  1. temperaturecooled to RT
  2. washwashed with water (4×180 mL) and brine (2×200 mL)
  3. dry with materialdried over MgSO4
  4. customEvaporation
  5. customgave a solid mass
  6. customThe crude product was triturated with EtOAc (10 mL)
  7. washwashed with EtOAc (10 mL)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-99f7e3347cdf4486862750b568d7426b
Source dataset
uspto-grants-2000_05
Patent number
US06066650

Reaction notes

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