2,6-Diisopropylphenyl isocyanate → HCID 54065611, compound

HRID 257799Notes

Reaction equation

HRID 257799 reaction equation
[CH:1]1([C:7]2([CH2:14][NH2:15])[O:11][C@H:10]([CH3:12])[C@@H:9]([CH3:13])[O:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:16][CH:17]([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]>C(OC(=O)C)C>[CH3:18][CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([CH3:26])[CH3:27])[C:20]=1[NH:28][C:29]([NH:15][CH2:14][C:7]1([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[O:11][C@H:10]([CH3:12])[C@@H:9]([CH3:13])[O:8]1)=[O:30])[CH3:16]

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 54424507HCID 54424507, compound

Product 1

HCID 54065611HCID 54065611, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of [(4R, 5R)-2-cyclohexyl-4,5-dimethyldioxolan-2-yl]methylamine (2.13 g 0.100 mole) in 40 ml of ethylacetate is added dropwise at room temperature 2,6-bis(1-methylethyl)phenylisocyanate (1.94 g 0.105 mole). The reaction mixture is stirred at room temperature for two hours. Volatiles are removed under reduced pressure and the residue is crystallized from ethylacetate/n-hexane, yielding 3.45 g of N-[2,6-bis(1-methylethyl)phenyl]-N'-[(4R,5R)-2-cyclohexyl-4,5-dimethyl-dioxolan-2-yl]methylurea, [α]D26 =-9.1 (C=0.653, AcOH).

Workup

  1. customVolatiles are removed under reduced pressure
  2. customthe residue is crystallized from ethylacetate/n-hexane

Sources & evidence

ORD record
ord-710d3557741146368291f62c8d52c529
Source dataset
uspto-grants-1993_11
Patent number
US05264441

Reaction notes

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