Hydrochloric Acid → HCID 58754842, compound

HRID 1711322Notes

Reaction equation

HRID 1711322 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=[C:9]([C:11]#[N:12])[N:10]=1)=[O:5])C.[OH-:21].[Na+].[OH-].[K+].Cl>CCO.O>[C:11]([C:9]1[N:10]=[C:6]([C:4]([OH:3])=[O:5])[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=1)(=[O:21])[NH2:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 67188254Ethyl 4-cyano-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 58754842HCID 58754842, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid ethyl ester (prepared in Example 11, step (c))(2.0 g, 6.8 mmol) in 15 mL of EtOH was added 5 N NaOH (2.0 mL, 10 mmol) and the reaction stirred for 8 h at RT. The mixture was concentrated, then water (20 mL) and 2 N KOH (3.4 mL, 6.8 mmol) was added and the mixture heated to 90° C. for 1 h. The mixture was cooled in an ice bath and the pH adjusted to 4 with 3 N HCl and a white ppt collected by filtration and dried under vacuum to give 1.5 g (77%) of the title compound. Mass spectrum (ESI, m/z): Calcd. for C1, H19N3O4Si, 286.1 (M+H), found 285.8.

Workup

  1. concentrationThe mixture was concentrated
  2. temperaturethe mixture heated to 90° C. for 1 h
  3. temperatureThe mixture was cooled in an ice bath
  4. filtrationa white ppt collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-42223e204a14424fad59abc5731e41fe
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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