2,6-Diisopropylphenyl isocyanate → HCID 22633534, compound

HRID 1532719Notes

Reaction equation

HRID 1532719 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:27])[CH3:26])[C:20]=1[N:28]=[C:29]=[O:30])([CH3:18])[CH3:17]>C(Cl)(Cl)Cl>[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:26])[CH3:27])[C:20]=1[NH:28][C:29](=[O:30])[N:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 22633584HCID 22633584, compound

Product 1

HCID 22633534HCID 22633534, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Lithium aluminium hydride (189 mg, 5 mmols) was added to an anhydride THF solution (7 ml) of the above amide (454 mg, 2 mmols), and the resulting mixture was refluxed for 2 hours under argon atmosphere. The reaction mixture was diluted with ether (30 ml), and an aqueous saturated solution of ammonium chloride (0.4 ml) was added to the mixture, and stirred for 30 minutes at room temperature, and dried with anhydrous potassium carbonate. And the mixture solution was filtered through a pad of Cerite. The filtrate was concentrated to obtain the residue, which was crystallized from ether and hexane, and 6-heptylamino-1-hexanol 223 mg (yield 52%) was obtained as colorless crystals. This amine (213 mg, 1 mmol) was added to a chloroform solution (2 ml) of 2,6-diisopropylphenylisocyanate (207 mg, 1 mmol), and stirred for 2 hours at room temperature. The solvent was evaporated, and the obtained residue was purified through silica gel column chromatography (silica gel 15 g, developer: chloroform:mrthanol=98:2). The resulting crystals were recrystallized from acetone-hexane to obtain 370 mg of N′-(2,6-di isopropylphenyl)-N-heptyl-N-(6-hydroxyhexyl)urea (yield: 88%) as colorless crystals.

Workup

  1. customThe solvent was evaporated
  2. customthe obtained residue was purified through silica gel column chromatography (silica gel 15 g, developer: chloroform:mrthanol=98:2)
  3. customThe resulting crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-89588aa0cc2a458d8e03517add899d59
Source dataset
uspto-grants-2001_03
Patent number
US06204278B1

Reaction notes

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