2,6-Diisopropylphenyl isocyanate → HCID 9935007, compound

HRID 374291Notes

Reaction equation

HRID 374291 reaction equation
[OH:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[C:4]([CH3:20])[CH:3]=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]>O1CCCC1.CN(C)C1C=CN=CC=1>[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:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:15])([CH3:16])[C:11]([O:13][CH3:14])=[O:12])=[C:4]([CH3:20])[CH:3]=1)=[O:35])[CH3:22]

Participants

5

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 86746388HCID 86746388, compound

Product 1

HCID 9935007HCID 9935007, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(4-hydroxy-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid, methyl ester, 1.5 g and 1.0 g (5 mmol) of 2,6-diisopropylphenylisocyanate in 75 mL of tetrahydrofuran containing 0.1 g of 4-dimethylaminopyridine is stirred at reflux for 18 hours overnight. The solvent is removed leaving 3.1 g of the title carbamate which crystallizes on standing. The crude precipitate is chromatographed on a 4.5 cm column containing 125 g of silica gel prepared in 1:1 hexane:dichloromethane. Elution with dichloromethane affords 1.8 g of the title compound. Recrystallization from 75 mL of hexane affords the title compound as a colorless solid; mp 111°-112° C.

Workup

  1. temperatureat reflux for 18 hours overnight
  2. customThe solvent is removed

Sources & evidence

ORD record
ord-bfd8717dd6f74d77bc858866bddf19bf
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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