1,4-Dichloro-cis-2-butene → 1,1'-(2z)-But-2-ene-1,4-diylbis{5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione}

HRID 468578Notes

Reaction equation

HRID 468578 reaction equation
[CH2:1]([N:27]1[C:31]([CH3:33])([CH3:32])[C:30](=[O:34])[N:29]([C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[C:37]([C:44]([F:47])([F:46])[F:45])[CH:36]=2)[C:28]1=[O:48])[CH2:2][CH2:3][CH2:4][N:5]1[C:9]([CH3:11])([CH3:10])[C:8](=[O:12])[N:7]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:14]=2)[C:6]1=[O:26].ClC/C=C\CCl>>[CH2:1]([N:27]1[C:31]([CH3:33])([CH3:32])[C:30](=[O:34])[N:29]([C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[C:37]([C:44]([F:47])([F:46])[F:45])[CH:36]=2)[C:28]1=[O:48])/[CH:2]=[CH:3]\[CH2:4][N:5]1[C:9]([CH3:11])([CH3:10])[C:8](=[O:12])[N:7]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([C:22]([F:25])([F:23])[F:24])[CH:14]=2)[C:6]1=[O:26]

Participants

3

Reactant 2

HCID 64321151,4-Dichloro-cis-2-buteneHCID 497638371,1'-Butane-1,4-diylbis{5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione}

Product 1

HCID 871352161,1'-(2z)-But-2-ene-1,4-diylbis{5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione}Yield 40%

Procedure

The experimental protocol used is the same as that described for the synthesis of the compound of Example 1, cis-1,4-dichloro-2-butene replacing 1.4 dibromobutane. The expected compound is obtained in the form of a pale yellow solid with a yield of 40%. Melting point: 191-193° C.

Sources & evidence

ORD record
ord-4b2fe6b5a50044c2aca6c0af38ce7a54
Source dataset
uspto-grants-2014_01
Patent number
US08624037B2

Reaction notes

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