Ethanol → HCID 19101525, compound

HRID 1974436Notes

Reaction equation

HRID 1974436 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:21]=[CH:20][C:9]([NH:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[C:22]([CH2:24][C:25](OCC)=[O:26])#[N:23].C([O-])(=O)C.[NH4+].C(O)C>O>[C:22]([C:24]1[C:25](=[O:26])[N:10]([C:9]2[CH:20]=[CH:21][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][CH:8]=2)[CH2:11][C:12]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[N:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 19101522HCID 19101522, compound

Product 1

HCID 19101525HCID 19101525, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

2-(4-Methanesulfonamidoanilino)acetophenone (5.0 g, 16.4 mmol), ethyl cyanoacetate (4.5 g, 39.4 mmol) and ammonium acetate (1.5 g, 19.5 mmol) were combined in a 100 mL round-bottomed flask equipped with a magnetic stir bar. The mixture was lowered into a pre-heated 140° C. oil bath, and became a stirrable melt within several minutes. Heating continued for 35 min during which time ethanol and water byproducts were observed boiling off, and a bright yellow solid formed amidst the dark supernatant. The reaction was removed from the heat and allowed to cool to 25° C. under vacuum. The crude material was stirred in ethanol (20 mL) for 30 min, then the product was collected by filtration, washed with more ethanol, and dried to yield 3.0 g (52%) as a bright yellow powder, m.p. 280° C. (dec). NMR and mass spectral data were consistent with the assigned structure. Elemental analysis: Calculated: C=61.18, H=4.28, N=11.89, S=9.07; Found: C=60.77, H=4.33, N=11.66, S=9.14.

Workup

  1. customequipped with a magnetic stir bar
  2. customwas lowered into a pre-heated 140° C.
  3. customwithin several minutes
  4. temperatureHeating
  5. customa bright yellow solid formed amidst the dark supernatant
  6. customThe reaction was removed from the
  7. temperatureheat
  8. filtrationthe product was collected by filtration
  9. washwashed with more ethanol
  10. customdried
  11. customto yield 3.0 g (52%) as a bright yellow powder, m.p. 280° C. (dec)

Sources & evidence

ORD record
ord-aca8361af26e4b6db3b94133512dbc62
Source dataset
uspto-grants-1994_02
Patent number
US05283165

Reaction notes

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