1,1'-Carbonyldiimidazole → 4-{[(Imidazole-1-carbonyl)-amino]-methyl}-2-methoxy-benzoic acid methyl ester

HRID 909106Notes

Reaction equation

HRID 909106 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[CH:6][C:5]=1[O:12][CH3:13].[C:15](N1C=CN=C1)([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=[O:16]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:15]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[O:16])=[CH:6][C:5]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67094960Methyl 4-(aminomethyl)-2-methoxybenzoate

Product 1

HCID 670953264-{[(Imidazole-1-carbonyl)-amino]-methyl}-2-methoxy-benzoic acid methyl esterYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-aminomethyl-2-methoxy-benzoic acid methyl ester (149 mg, 0.763 mmol) in N,N-dimethyl formamide (4.0 mL) was added 1,1′-carbonyldiimidazole (Aldrich, 127 mg, 0.762 mmol). After it was stirred at rt for 16 hrs under an argon atmosphere, the reaction mixture was extracted with EtOAc, and washed with water (2×), and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give 4-{[(imidazole-1-carbonyl)-amino]-methyl}-2-methoxy-benzoic acid methyl ester (224.3 mg, 101% crude) which was used without further purification.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washwashed with water (2×), and saturated NaCl
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6a767bbc3db04fafba9821c02162003f
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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