Citric Acid → HCID 68734627, compound

HRID 2089274Notes

Reaction equation

HRID 2089274 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20]([NH2:22])=[O:21])=[CH:14][CH:13]=1)([O-])=O.C[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCO.CN(C=O)C.O>[N:10]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:1][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20]([NH2:22])=[O:21])=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 68737933HCID 68737933, compound

Product 1

HCID 68734627HCID 68734627, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[(2-nitro-phenylamino)-methyl]-phenylbenzamide (14) (74.9 mmol) in anhydrous EtOH and anhydrous DMF (75 mL) was slowly added sodium methoxide (30% w/w) (375 mmol) at room temperature under argon atmosphere, followed by heating to 60° C. for 2 h. After cooling to ambient termperature, the solution was diluted with water (700 mL) and then acidified with saturated citric acid. The resulting precipitate was collected on a sintered funnel while rinsing with water. The crude product was recrystallized in hot EtOH.

Workup

  1. customat room temperature
  2. temperatureAfter cooling to ambient termperature
  3. customThe resulting precipitate was collected on a sintered funnel
  4. washwhile rinsing with water
  5. customThe crude product was recrystallized in hot EtOH

Sources & evidence

ORD record
ord-72129b9ea5e3402095874e170f4b71e2
Source dataset
uspto-grants-2013_05
Patent number
US08436031B2

Reaction notes

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