Hexane → 4-(3-t-Butylureidomethyl)-1-aminomethylbenzene

HRID 483925Notes

Reaction equation

HRID 483925 reaction equation
[C:1]1([CH2:9][NH2:10])[CH:6]=[CH:5][C:4]([CH2:7][NH2:8])=[CH:3][CH:2]=1.CCCCCC.[C:17]([N:21]=[C:22]=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:17]([NH:21][C:22](=[O:23])[NH:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH2:9][NH2:10])=[CH:2][CH:3]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8058HexaneHCID 62412tert-Butyl isocyanateHCID 683151,4-Benzenedimethanamine

Product 1

HCID 200967404-(3-t-Butylureidomethyl)-1-aminomethylbenzeneYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.7 g p-xylylenediamine in 100 ml methylene dichloride, was added slowly with stirring 10 ml of a n-hexan solution containing 990 mg t-butyl isocyanate under ice cooling. Stirring was continued at room temperature for two hours, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography, giving 1 g of 4-(3-t-butylureidomethyl)-1-aminomethylbenzene.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ed4449f4d3c24a34ad09ba7e4296ac68
Source dataset
uspto-grants-1993_07
Patent number
US05227492

Reaction notes

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