Tert-Butyl nitrite → Ethyl 1-phenylimidazole-4-carboxylate

HRID 842699Notes

Reaction equation

HRID 842699 reaction equation
N(OC(C)(C)C)=O.[CH2:8]([O:10][C:11]([C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:23]=[CH:22][C:21](N)=[CH:20][CH:19]=2)[CH:17]=1)=[O:12])[CH3:9]>CN(C)C=O.[Cl-].[Na+].O>[CH2:8]([O:10][C:11]([C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=1)=[O:12])[CH3:9]

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 18726772ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylate

Product 1

HCID 11469974Ethyl 1-phenylimidazole-4-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

Tert-butyl nitrite (535 mg, 5.19 mmol) in dry dimethylformamide (15 ml) was heated to 65° C. under nitrogen and then 1-(4-aminophenyl)imidazole-4-carboxylic acid ethyl ester (see part (ii)) (800 mg, 3.463 mmol) in dry dimethylformamide (5 ml) was added over 10 minutes. The mixture was heated at 65° C. for a further 20 minutes and then cooled to room temperature. The mixture was poured into saturated brine (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with dichloromethane gave the title compound (520 mg, 70%) as an off-white solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane (3×20 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-105b8ddd5cf5468f84e89b99f52d2efc
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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