Hydrochloric Acid → HCID 58425472, compound

HRID 1481524Notes

Reaction equation

HRID 1481524 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH3:14])[CH:7]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:9]=1)=[O:4].[OH-].[Na+].Cl>CO>[C:10]([C:8]1[N:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]([CH3:14])[CH:7]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67410811HCID 67410811, compound

Product 1

HCID 58425472HCID 58425472, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-tert-butyl-1-methyl-1H-imidazole-2-carboxylic acid methyl ester (680 mg, 3.46 mmol, prepared as described in the previous step) and 1N NaOH (3.81 mL, 3.81 mmol) in MeOH (10 mL) was stirred at room temperature for 2 h. To the resulting mixture was then added 1.0 N aqueous HCl (3.85 mL). The solvent was removed under reduced pressure and the residue was treated with DCM (50 mL). The solid was filtered off through diatomaceous earth and washed with DCM. The combined organic layers were dried with Na2SO4 and concentrated in vacuo to yield 4-tert-butyl-1-methyl-1H-imidazole-2-carboxylic acid as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 7.00 (s, 1H), 4.18 (s, 3H), 1.49 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C9H14N2O2: 183.1 (M+H). Measured: 183.1.

Workup

  1. customprepared
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was treated with DCM (50 mL)
  4. filtrationThe solid was filtered off through diatomaceous earth
  5. washwashed with DCM
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-932b28d77dd24228838ba1d62b80c502
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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