Diethyl Phthalate → HCID 178469628, compound

HRID 496582

Reaction equation

HRID 496582 reaction equation
[C:1]1([N:7]2[C:11]([NH:12][CH:13]=[C:14]([C:20]([O:22]CC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=O)C1C(=CC=CC=1)C(OCC)=O>CCCCCC>[OH:22][C:20]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[CH:9][C:10]=12

Participants

4

Reactant 2

HCID 6781Diethyl PhthalateHCID 22322171HCID 22322171, compound

Product 1

HCID 178469628HCID 178469628, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 18.1 g. (0.055 mole) of diethyl {[(1-phenyl-5-pyrazolyl)amino]methylene}malonate and 150 ml of diethyl phthalate was heated at 240-250° for 1 hour. The mixture was chilled and diluted with hexane. Chilling and filtering gave crystals which were washed with hexane and with hexane-ethanol (1:1) to give 11 g. (70%) of off white crystals, m.p. 149-150° C. From a similar small scale run 1.75 g. was recrystallized from 110 ml. of ethanol to give 1.58 g. of off white crystals, m.p. 149-150° C.

Workup

  1. additionA mixture of 18.1 g
  2. temperatureThe mixture was chilled
  3. temperatureChilling
  4. filtrationfiltering
  5. customgave crystals which
  6. washwere washed with hexane and with hexane-ethanol (1:1)
  7. customto give 11 g
  8. customwas recrystallized from 110 ml
  9. customof ethanol to give 1.58 g

Sources & evidence

ORD record
ord-dc4ccf8946e84489879723fc8a8c847c
Source dataset
uspto-grants-2005_09
Patent number
US06946473B2

Linked notes

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