N-Methyl-1-naphthylamine → N-Methyl-N-naphthalen-1-yl-N'-[2-(pyridin-2-yl)ethyl]urea

HRID 436377Notes

Reaction equation

HRID 436377 reaction equation
[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH2:20][N:21]=[C:22]=[O:23]>O1CCCC1>[CH3:1][N:2]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[C:22](=[O:23])[NH:21][CH2:20][CH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=1

Participants

4

Reactant 2

HCID 16667N-Methyl-1-naphthylamineHCID 545025452-(2-Isocyanatoethyl)pyridine

Product 1

HCID 54162662N-Methyl-N-naphthalen-1-yl-N'-[2-(pyridin-2-yl)ethyl]urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3.14 gm. (0.02 mole) of N-methyl-1-naphthylamine in 75 ml. of tetrahydrofuran there is added 2.96 gm. (0.02 mole) of 2-pyridylethylisocyanate with stirring. After 30 minutes of stirring at ambient temperature, the mixture is refluxed for 1 hour. The solvent is then removed in vacuo and the residue crystallized from alcohol-water (4:1 v/v) to furnish 3-methyl-3-(1-naphthyl)-1-(2-pyridylethyl)urea.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. customThe solvent is then removed in vacuo
  3. customthe residue crystallized from alcohol-water (4:1 v/v)

Sources & evidence

ORD record
ord-ebe76d0769914609bda99d57d38e219e
Source dataset
uspto-grants-1977_02
Patent number
US04008326

Reaction notes

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