1,1'-Carbonyldiimidazole → HCID 59473790, compound

HRID 2069836Notes

Reaction equation

HRID 2069836 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:11]=[C:10]([CH3:12])[C:6]([C:7](O)=[O:8])=[C:5]([F:13])[CH:4]=1.C(N1C=CN=C1)([N:17]1C=CN=C1)=O>C1COCC1>[CH3:1][N:2]([CH3:14])[C:3]1[CH:11]=[C:10]([CH3:12])[C:6]([C:7]([NH2:17])=[O:8])=[C:5]([F:13])[CH:4]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59473815HCID 59473815, compound

Product 1

HCID 59473790HCID 59473790, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-Dimethylamino-2-fluoro-6-methyl-benzoic acid (0.896 g, 4.54 mmol) in THF (11 mL) was added carbonyldiimidazole (0.958 g, 5.91 mmol). The solution became homogeneous with bubbling. After 30 min., this solution was added to concentrated ammonium hydroxide (7 mL), and the solution became cloudy. Following removal of solvent after 1 h, the residue was taken up in H2O and filtered to give 4-dimethylamino-2-fluoro-6-methyl-benzamide as a white solid (0.696 g, 78%).

Workup

  1. customwith bubbling
  2. additionthis solution was added to concentrated ammonium hydroxide (7 mL)
  3. customremoval of solvent after 1 h
  4. filtrationfiltered

Sources & evidence

ORD record
ord-34ccfe6ec1d646e78c46668e095839e0
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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