Veratraldehyde → HCID 178488768, compound

HRID 706313Notes

Reaction equation

HRID 706313 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH:16]=O.[Si](C#N)(C)(C)C.[N:29]1([C:34](N2C=CN=C2)=[O:35])C=CN=[CH:30]1>[Pd]>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[CH:16]([C:15]4[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:13]([O:12][CH3:11])[CH:14]=4)[CH2:30][NH:29][C:34]3=[O:35])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 8419VeratraldehydeHCID 682631,1'-CarbonyldiimidazoleHCID 82115Trimethylsilyl cyanideHCID 178507353HCID 178507353, compound

Product 1

HCID 178488768HCID 178488768, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The compound was synthesized starting from 1H-benzo[d]imidazol-5-amine (0.400 g, 3 mmol), 3,4-dimethoxybenzaldehyde (0.5 g, 3 mmol), TMSCN (0.375 mL, 3 mmol), Pd/C (10%, 0.02 g), TEA 1.05 mL, 7.5 mmol), di-(imidazol-1-yl)methanone (0.730 g, 4.5 mmol) as described in method 2 to give 1-(1H-benzo[d]imidazol-5-yl)-5-(3,4-dimethoxyphenyl)imidazolidin-2-one (yield: 0.3 g, 0.89 mmol, 29.7%). Treating with borontribromide (0.505 mL, 5.34 mmol) as described for example 151 gives the title compound.

Workup

  1. customThe compound was synthesized

Sources & evidence

ORD record
ord-1604a808738a4a92a49990739e0c8a65
Source dataset
uspto-grants-2015_11
Patent number
US09173885B2

Reaction notes

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