Toluene → HCID 67497844, compound

HRID 1919555Notes

Reaction equation

HRID 1919555 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.[CH2:27]([N:34]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][NH:40][CH3:41])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:49]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][CH3:49])=[O:19])[C:11]3[C:10](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:9]=[C:8]2[N:40]([CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][N:34]([CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:41])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 59322472HCID 59322472, compoundHCID 86641596HCID 86641596, compound

Product 1

HCID 67497844HCID 67497844, compound

Procedure

To a solution of methyl 3-[2-(4-biphenylyliminomethyleneamino)phenyl]acrylate (11) (1.12 g, 3.15 mmol) in toluene (100 ml) was added N,N-dibenzyl-N′-methylpentane-1,5-diamine (18) (1.87 g, 6.30 mmol). Then, the reaction mixture was stirred for 2 hours and extracted with dichloromethane three times. 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: ethyl acetate:hexane:dichloromethane=1:2:1) to give the target compound as a yellow liquid (2.56 g, quantitative yield).

Workup

  1. extractionextracted with dichloromethane three times
  2. dry with materialThe combined organic phase was dried with anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c6ed02c4222e443dae00ed429966a81e
Source dataset
uspto-grants-2012_05
Patent number
US08168646B2

Reaction notes

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