Hexane → HCID 57617105, compound

HRID 2045697Notes

Reaction equation

HRID 2045697 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][C:11]([O:13]CC)=O)=[CH:4][C:3]=1[O:22][CH3:23].CCCCCC>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:22][CH3:23])[NH:8][C:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:10][C:11]2=[O:13]

Participants

4

Reactant 2

HCID 8058HexaneHCID 58005168Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate

Product 1

HCID 57617105HCID 57617105, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent3×

Procedure

DOWTHERM A (450 mL) was heated to reflux (˜300 C). A mixture of the product from step 2 (49 g, 130 mmol) in DOWTHERM A (50 mL) was added to the heated DOWTHERM A solution portionwise. The mixture was stirred at reflux for 30 min after the addition was complete. The mixture was cooled RT, and hexane (400 mL) was added. The mixture was stirred for 30 min and filtered, and the solids were washed with hexane to give the title compound (38 g, 88% yield). LRMS (M+H)+ Calcd.: 330.0; found 330.2.

Workup

  1. temperatureto reflux (˜300 C)
  2. temperatureat reflux for 30 min
  3. additionafter the addition
  4. stirringThe mixture was stirred for 30 min
  5. filtrationfiltered
  6. washthe solids were washed with hexane

Sources & evidence

ORD record
ord-d0bbaba9470b47b2b146dfb92ba4ccee
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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