1,1'-Carbonyldiimidazole → HCID 67095593, compound

HRID 909113Notes

Reaction equation

HRID 909113 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[C:13](N1C=CN=C1)([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:14]>CN(C)C=O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([NH:1][C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[O:14])=[CH:3][C:4]=1[CH3:12]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 11672721Methyl 4-amino-2-methylbenzoate

Product 1

HCID 67095593HCID 67095593, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 4-amino-2-methylbenzoate (208.9 mg, 1.230 mmol) in N,N-dimethyl formamide (5 mL) was added 1,1′-carbonyldiimidazole (Aldrich, 215 mg, 1.29 mmol). After it was stirred at rt overnight 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]-2-methyl-benzoic acid methyl ester (342.0 mg) 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-65ba083b94074376a404e41a9df4b71a
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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