2,6-Diisopropylphenyl isocyanate → HCID 20068729, compound

HRID 981904Notes

Reaction equation

HRID 981904 reaction equation
[C:1]1([C:7]2(N(C)CCCCCCC)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[N:33]=[C:34]=[O:35])([CH3:23])[CH3:22]>C(OCC)(=O)C>[CH3:23][CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:31])[CH3:32])[C:25]=1[NH:33][C:34](=[O:35])[N:33]([CH2:25][CH2:24][CH2:29][CH2:28][CH2:27][CH2:26][CH3:30])[CH2:34][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1)[CH3:22]

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 54134860HCID 54134860, compound

Product 1

HCID 20068729HCID 20068729, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1-Phenylcyclopentyl-N-heptylmethylamine (5.46 g; 0.02M) was dissolved in 75 mL of ethyl acetate. To this solution was added, with stirring, a solution of 2,6-diisopropyl phenyl isocyanate (4.06 g; 0.02M) in 25 mL of ethyl acetate. The reaction mixture was stirred at room temperature overnight, concentrated to dryness, and the resulting white solid was chromatographed on silica using hexane:ethyl acetate (8:2) as the eluant to yield 5.2 g of the title compound, mp 95-97° C.

Workup

  1. additionTo this solution was added
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. concentrationconcentrated to dryness
  4. customthe resulting white solid was chromatographed on silica

Sources & evidence

ORD record
ord-dea7017bacf84aa2908756de912fa4b9
Source dataset
uspto-grants-1991_02
Patent number
US04994465

Reaction notes

Loading…