Chlorotrimethylsilane → 4-Amino-1-(3,4-dimethoxybenzyl)-5-imidazolecarboxamide

HRID 382386Notes

Reaction equation

HRID 382386 reaction equation
[CH2:1](O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.C[Si](Cl)(C)C.C(=[N:25][C:26]1[N:27]=[CH:28][NH:29][C:30]=1[C:31]([NH2:33])=[O:32])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CS(C)=O>[NH2:25][C:26]1[N:27]=[CH:28][N:29]([CH2:1][C:2]2[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=2)[C:30]=1[C:31]([NH2:33])=[O:32]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7118Veratryl alcoholHCID 11430Potassium CarbonateHCID 539704464-Benzylideneamino-5-imidazolecarboxamide

Product 1

HCID 183603764-Amino-1-(3,4-dimethoxybenzyl)-5-imidazolecarboxamideYield 63%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A dimethyl sulfoxide solution of 4.29 ml (30 mmol) veratryl alcohol (3,4-dimethoxybenzyl alcohol) was treated in 22.86 ml (180 mmol) trimethylsilyl chloride at room temperature for 1 hour. The resulting product was dissolved in ethyl acetate, washed with distilled water and saturated brine, and dried over anhydrous magnesium sulfate. After concentration under vacuum, the resulting residue was reacted with 2.14 g (10 mmol) of 4-benzylideneamino-5-imidazole carboxamide and 5.52 (40 mmol) of potassium carbonate in the same manner as in Reference Example 2 to obtain 1.73 g of 4-amino-1-(3,4-dimethoxybenzyl)-5-imidazolecarboxamide (yield 63%).

Workup

  1. washwashed with distilled water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationAfter concentration under vacuum

Sources & evidence

ORD record
ord-ad5194c48b8c4212bf0f5c6c99faa529
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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