Dimethylhydantoin → 5,5-Dimethyl-3-{4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzyl}-imidazolidine-2,4-dione

HRID 2100691Notes

Reaction equation

HRID 2100691 reaction equation
[CH3:1][C:2]1[C:3]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)=[CH2:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.CS(Cl)(=O)=O.[CH3:31][C:32]1([CH3:39])[NH:36][C:35](=[O:37])[NH:34][C:33]1=[O:38].[H-].[Na+]>CCN(CC)CC>[CH3:31][C:32]1([CH3:39])[NH:36][C:35](=[O:37])[N:34]([CH2:24][C:21]2[CH:22]=[CH:23][C:18]([C:16]([C:3]3[C:2]([CH3:1])=[CH:11][C:10]4[C:9]([CH3:13])([CH3:12])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]=4[CH:4]=3)=[CH2:17])=[CH:19][CH:20]=2)[C:33]1=[O:38]

Participants

6

Reactant 4

HCID 6491DimethylhydantoinHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 57799975{4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl}-methanol

Product 1

HCID 114081715,5-Dimethyl-3-{4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzyl}-imidazolidine-2,4-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Adopting the procedure outlined for example 9 using 40.0 mg (0.12 mmol) of {4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-phenyl}-methanol, 0.05 mL of methanesulfonyl chloride, 0.10 mL of NEt3, 300 mg of 5,5-dimethylhydantoin, and 56 mg of NaH, 32.0 mg of the product was obtained.

Sources & evidence

ORD record
ord-03888127d35449a49defe70ba28941de
Source dataset
uspto-grants-2009_08
Patent number
US07572816B2

Reaction notes

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