N-Methylaniline → HCID 86660684, compound

HRID 1918443Notes

Reaction equation

HRID 1918443 reaction equation
C1(OC(=NC2C=CC=CC=2)C=COC2C=CC=CC=2)C=CC=CC=1.[CH3:25][N:26]([CH:33]=[CH:34][C:35](=[N:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CNC1C=CC=CC=1>C(#N)C>[CH3:25][N:26]([CH:33]=[CH:34][C:35](=[N:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[O:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 86686875Phenyl 3-(N'-methyl-N'-phenylamino)-N-phenylacrylimidate phenyl 3-(phenoxy)-N-phenylacrylimidate

Product 1

HCID 86660684HCID 86660684, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phenyl 3-(N′-methyl-N′-phenylamino)-N-phenylacrylimidate phenyl 3-(phenoxy)-N-phenylacrylimidate (0.39 g) was dissolved to acetonitrile (5 ml), and N-methylaniline (0.20 g) and catalytic amount of N,N-dimethylaminopyridine were added at room temperature. It was stirred for two hours at the same temperature and for eight hours under heat refluxing. It was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain phenyl 3-(N′-methyl-N′-phenylamino)-N-phenylacrylimidate (0.17 g) as light brown crystal.

Workup

  1. additionwere added at room temperature
  2. temperatureunder heat
  3. temperaturerefluxing
  4. concentrationIt was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c9363a88299e45af9036740f93d8354c
Source dataset
uspto-grants-2013_12
Patent number
US08618329B2

Reaction notes

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