Toluene → HCID 25112244, compound

HRID 1919554Notes

Reaction equation

HRID 1919554 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[N:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]=[CH:17][C:18]([O-:20])=[O:19])=[CH:3][CH:2]=1.[CH3:27][NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.[C:39]1(C)C=CC=CC=1>>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([N:7]2[CH:16]([CH2:17][C:18]([O:20][CH3:39])=[O:19])[C:11]3[C:10](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:9]=[C:8]2[N:28]([CH3:27])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][N:34]2[CH2:35][CH2:36][CH2:37][CH2:38]2)=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 62440092HCID 62440092, compoundHCID 86641596HCID 86641596, compound

Product 1

HCID 25112244HCID 25112244, compoundYield 52%

Procedure

To a solution of 3-[2-(4-biphenylyliminomethyleneamino)phenyl]acrylate (11) (0.83 g, 2.35 mmol) in toluene (50 ml) was slowly added N-methyl-N-[5-(pyrrolidin-1-yl)pentyl]amine (6) obtained in Example 5 (0.80 g, 4.70 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 1 hour. After the reaction was completed, the resulting reaction mixture was extracted with a saturated 1N NaOH aqueous solution and dichloromethane three times. Then, the combined organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: dichloromethane:methnol:ammonia water=100:9:1) to give the target compound (0.63 g, 52%).

Workup

  1. customat 0° C.
  2. customthe resulting reaction mixture
  3. extractionwas extracted with a saturated 1N NaOH aqueous solution and dichloromethane three times
  4. dry with materialThen, the combined organic phase was dried with anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-b4b652ae0fa9423cb0f6cf272a88ccfd
Source dataset
uspto-grants-2012_05
Patent number
US08168646B2

Reaction notes

Loading…