Acetic Acid → HCID 53643628, compound

HRID 1274290Notes

Reaction equation

HRID 1274290 reaction equation
[CH:1]([C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:4]=1)=O.[C:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])#[N:25].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1>[NH2:23][S:20]([C:17]1[CH:16]=[CH:15][C:14]([N:5]2[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:7][C:3]([CH:1]=[C:26]([C:24]#[N:25])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:4]2)=[CH:19][CH:18]=1)(=[O:21])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 12082818HCID 12082818, compound

Product 1

HCID 53643628HCID 53643628, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the aldehyde from Step 1 (1.2 g, 3.6 mmol) in benzene (18 mL) was added ethyl cyanoacetate (0.38 mL, 3.6 mmol), ammonium acetate (50 mg, 0.7 mmol) and glacial acetic acid (0.17 mL, 2.8 mmol). The solution was heated at reflux for 18 hours, cooled, and partitioned between water and ethyl acetate. The organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine. The organic solution was dried and concentrated. The residue was chromatographed on silica (40% hexane in ethyl acetate) to give the desired product (1.0 g, 66%): Anal. calc'd for C21H18N4O4S: C, 59.82; H, 4.30; N, 13.22. Found: C, 59.70; H, 4.29; N, 13.26.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 18 hours
  3. temperaturecooled
  4. custompartitioned between water and ethyl acetate
  5. washThe organic solution was washed with a saturated aqueous sodium bicarbonate solution, water and brine
  6. customThe organic solution was dried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica (40% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-230494cb5ef74a4a97f517bd45321302
Source dataset
uspto-grants-2000_12
Patent number
US06156781

Reaction notes

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