1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178469613, compound

HRID 2104473Notes

Reaction equation

HRID 2104473 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14]CC)=O.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CCCCCC>[CH2:20]([O:19][C:17]([C:11]1[CH:10]=[N:9][C:4]2[C:5]([C:12]=1[OH:14])=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:1])([F:22])[F:23])=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 3107365Diethyl 2-{[2-(trifluoromethyl)anilino]methylene}malonate

Product 1

HCID 178469613HCID 178469613, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
250 °C

Procedure

Diethyl 2-({[2-(trifluoromethyl)phenyl]amino}methylene)malonate (compound of formula (IV)), 69.73 g, 210.5 mmol) was taken into Dowtherm A (350 mL) and brought to reflux (˜250° C.) with the removal of ethanol that was formed during the reaction for 45 min. The reaction was allowed to cool to approximately 100° C. then carefully poured into hexane (1 L) and allowed to cool overnight. A white solid precipitated which was filtered and dried to afford the title compound as a white solid (55.04 g, 91.7%). MS ESI (m/z) 286 ([M+H]+); MS ESI (m/z) 284 ([M−H]−).

Workup

  1. customwith the removal of ethanol that
  2. customwas formed during the reaction for 45 min
  3. temperatureto cool to approximately 100° C.
  4. temperatureto cool overnight
  5. customA white solid precipitated which
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-d33ee1d9ceff4f018fdba3483bb0c3ce
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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