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

HRID 374374

Reaction equation

HRID 374374 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-284a5578654e45f49e0ae5dd23284035
Source dataset
uspto-grants-1992_11
Patent number
US05166429

Linked notes

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