Hexane → HCID 57617105, compound

HRID 389187Notes

Reaction equation

HRID 389187 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×

Conditions

Temperature
300 °C

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 portionwise, and the mixture stirred at reflux for 30 minutes after addition was complete. The mixture was cooled to RT; hexane (400 mL) was added; and the mixture was stirred for 30 minutes, filtered, and the solids washed with hexane to give the title compound (38 g). LRMS (M+H)+ Calcd.: 330.0; found 330.2.

Workup

  1. temperatureat reflux for 30 minutes
  2. additionafter addition
  3. temperatureThe mixture was cooled to RT
  4. stirringand the mixture was stirred for 30 minutes
  5. filtrationfiltered
  6. washthe solids washed with hexane

Sources & evidence

ORD record
ord-2b3a735fff97402f98584df7c705a2c4
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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