m-Tolyl isocyanate → 2-(3-Methylphenylaminocarbonylamino)eth-1-ylamine

HRID 1072468Notes

Reaction equation

HRID 1072468 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3]C(C)(C)C)=O.[C:12]1([CH3:21])[CH:17]=[CH:16][CH:15]=[C:14]([N:18]=C=O)[CH:13]=1>C(#N)C>[CH3:21][C:12]1[CH:13]=[C:14]([NH:18][C:1]([NH:8][CH2:9][CH2:10][NH2:11])=[O:3])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 187201N-BOC-ethylenediamine

Product 1

HCID 221388592-(3-Methylphenylaminocarbonylamino)eth-1-ylamineYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Boc-Ethylene diamine (800 mg, 5 mmol) and m-tolyl isocyanate (665 mg, 5 mmol) were dissolved in acetonitrile and the mixture stirred at room temperature for 4 hrs. Solvent was removed under reduced pressure and the residue absorbed onto silica gel; prior to purification by flash column chromatography (silica, hexane:EtOAc 1:1) to yield the desired compound as a white solid (300 mg, 21%) (MS (+ESI, m/e) 294 (M+H)+). The N-Boc protected compound (300 mg, 1.02 mmol) was dissolved in formic acid (10 ml) and the mixture stirred at room temperature overnight. Excess acid was removed to yield the formate salt of the title compound as a white foam (210 mg).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue absorbed onto silica gel
  3. customprior to purification by flash column chromatography (silica, hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-68da05a6cc8f4c16a50c035ae1ec48ec
Source dataset
uspto-grants-2005_06
Patent number
US06911439B2

Reaction notes

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