Aniline → 3-Methylthiophene-2-aldehyde phenylimine

HRID 1081963Notes

Reaction equation

HRID 1081963 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCCCCC>[C:10]1([N:9]=[CH:7][C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 799113-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 9273143-Methylthiophene-2-aldehyde phenylimineYield 85%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

3-methylthiophene-2-aldehyde (103 g, 0.816 mol) was mixed with hexane (100 ml), to which aniline (74.4 ml, 0.816 mol) was added and stirred at room temperature for 7 hours. After separating deposited crystalline solids by filtration, and washing with hexane, 139.5 g (yield: 85%) of 3-methylthiophene-2-aldehyde phenylimine was obtained. After concentrating the liquid filtrate and stirring at room temperature for a further 12 hours, 7.30 g (yield: 4%) of 3-methylthiophene-2-aldehyde phenylimine was obtained by post treatment in the same manner as above. 1H-NMR spectra (chemical shift, ppm: in CDCl3); 2.47 (3H, s), 6.92 (1H, d, J=4.9 Hz), 7.15-7.30 (3H), 7.30-7.45 (3H), 8.61 (1H).

Workup

  1. additionwas added
  2. customAfter separating
  3. filtrationby filtration
  4. washwashing with hexane

Sources & evidence

ORD record
ord-b84c1d3532dc4c3fbbe53fadb73e3e39
Source dataset
uspto-grants-1996_12
Patent number
US05587486

Reaction notes

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