n-Heptyl isocyanate → HCID 23370089, compound

HRID 1901044Notes

Reaction equation

HRID 1901044 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1.[CH2:19]([N:26]=[C:27]=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>ClCCl>[CH3:13][N:12]([CH3:14])[C:9]1[CH:10]=[CH:11][C:6]([N:5]([CH2:4][C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[NH:1][C:27]([NH:26][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:28])[C:27]([NH:26][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:28])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 138341n-Heptyl isocyanateHCID 23370100HCID 23370100, compound

Product 1

HCID 23370089HCID 23370089, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-aminobenzyl)-N',N'-dimethyl-1,4-phenylenediamine (0.6 g) in dichloromethane (10 ml) was added under ice-cooling heptyl isocyanate (0.4 g) and the mixture was stirred overnight while returning slowly to room temperature. The solvent was distilled off and the residue was purified by a silica gel column chromatography (chloroform:ethyl acetate=20:1) to give 1-(4-dimethylaminophenyl)-1-[2-(3-heptylureido)benzyl]-3-heptylurea as a non-crystallizable solid (0.55 g, 44%).

Workup

  1. customwhile returning slowly to room temperature
  2. distillationThe solvent was distilled off
  3. customthe residue was purified by a silica gel column chromatography (chloroform:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-04073d6b2ce64c83973c16701f16e06a
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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