Carbonic acid-guanidine (1:1) → HCID 86695818, compound

HRID 1052002Notes

Reaction equation

HRID 1052002 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13](=O)[C:12](=[CH:17]N(C)C)[CH2:11]2)=[CH:6][CH:5]=1.[C:22](=O)(O)O.[NH2:26][C:27]([NH2:29])=[NH:28].O.O.O.C([O-])(=O)C.[Na+]>CCO>[CH2:1]([O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13]3[N:28]=[C:27]([NH2:29])[N:26]=[CH:17][C:12]=3[CH2:11]2)=[CH:6][CH:5]=1)[CH3:22]

Participants

5

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 23665404Sodium Acetate TrihydrateHCID 86695817HCID 86695817, compound

Product 1

HCID 86695818HCID 86695818, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl-4-(3-dimethylaminomethylene-4-oxopiperidin-1-yl)-benzoate (3.00 g, 10.40 mmol) in EtOH (200 mL) was treated with guanidine carbonate (7.50 g, 41.60 mmol), followed by sodium acetate trihydrate (11.32 g, 83.20 mmol). The reaction mixture was refluxed for 16 hours and allowed to cool to room temperature. The insolubles were filtered off and the filtrate was concentrated. The residue was partitioned between water and ethyl acetate and the solid was filtered off, washed with water, ethyl acetate, and dried to give the title compound (258 mg). The filtered insoluble material from the reaction mixture was suspended in water, stirred for 30 minutes, and the remaining light yellow, amorphous solid was collected, washed with water, ethyl acetate, and dried to give an additional amount of the title compound (1.95 g, total yield 71%).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. filtrationThe insolubles were filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was partitioned between water and ethyl acetate
  5. filtrationthe solid was filtered off
  6. washwashed with water, ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-e5edc64e2aed472ab786a5fd47a20fcb
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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