Diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate → HCID 178469631, compound

HRID 2268041Notes

Reaction equation

HRID 2268041 reaction equation
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[N:17]([CH2:18][CH3:19])[N:16]=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[C:4]([OH:20])=[C:14]2[CH:15]=[N:16][N:17]([CH2:18][CH3:19])[C:13]2=[N:12][CH:11]=1)=[O:7])[CH3:10]

Participants

3

Reactant 1

HCID 12845080Diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate

Product 1

HCID 178469631HCID 178469631, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

(1-Ethylpyrazol-5-yl-amino)methylenemalonate diethyl ester (180 mmol from previous reaction) was dissolved in diphenyl ether (200 mL), and the resulting solution was placed in a preheated oil bath at 255° C. The reaction solution was heated for 5 h, and then the diphenyl ether was removed via distillation. The resulting brown reaction mixture was cooled to room temperature and poured to hexane (1 L). Cooling this solution to −78° C., followed by filtration of the resulting precipitate afforded the title compound as a beige colored needle shaped solid that was >90% pure by HPLC and was used directly (25 g, 60% for 2 steps). A portion was recrystallized using ethanol-H2O to afford a white solid: mp 85-86° C.; LRMS (m/z) 236 (MH+).

Workup

  1. customthe resulting solution was placed in a preheated oil bath at 255° C
  2. temperatureThe reaction solution was heated for 5 h
  3. customthe diphenyl ether was removed via distillation
  4. additionpoured to hexane (1 L)
  5. temperatureCooling this solution to −78° C.
  6. filtrationfollowed by filtration of the resulting precipitate

Sources & evidence

ORD record
ord-9b58b456605d46548caf66f49f6918f2
Source dataset
uspto-grants-2001_12
Patent number
US06326379B1

Reaction notes

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