Hydrochloric Acid → HCID 58425472, compound

HRID 1191189Notes

Reaction equation

HRID 1191189 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-c58a78b0d14648619a2d5311bc5598d1
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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