Citric Acid → HCID 68734627, compound

HRID 2089275Notes

Reaction equation

HRID 2089275 reaction equation
[NH2:1]N1C2C([N+]([O-])=O)=CC=CC=2N=C1O.[CH3:15][C:16]([CH3:21])(C)[C:17](Cl)=[O:18].[N+]([C:25]1[CH:26]=[CH:27][C:28]2[N:32]=[C:31]([C:33]3[CH:38]=[CH:37][C:36](N)=[CH:35][CH:34]=3)[N:30](O)[C:29]=2[CH:41]=1)([O-])=O.[C:42](O)(=O)[CH2:43][C:44](CC(O)=O)(C(O)=O)O>N1C=CC=CC=1.[OH-].[Na+].O>[N:30]1[C:29]2[CH:41]=[CH:25][CH:26]=[CH:27][C:28]=2[NH:32][C:31]=1[C:33]1[CH:38]=[CH:37][C:36]([C:15]2[CH:44]=[CH:43][CH:42]=[CH:21][C:16]=2[C:17]([NH2:1])=[O:18])=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 62493Pivaloyl chlorideHCID 10423236HCID 10423236, compoundHCID 178514278HCID 178514278, compound

Product 1

HCID 68734627HCID 68734627, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-aminonitrobenzoimidazolol (17) (1.00 mmol) in anhydrous pyridine (2.0 mL) was added acid chloridesa (2.5 mmol) or the in situ mixed anhydrides at room temperature. (The mixed anhydride was prepated by adding trimethylacetyl chloride (2.5 mmol) dropwise to a solution of the carboxylic acid (2.55 mmol) in anhydrous pyridine at 0° C., After 1 hour, 6-nitro-2-(-4-aminophenyl)-1-hydroxybenzimidazole was added in one portion.) After stirring for 2-3 h at room temperature, the solution was diluted with 3M NaOH (6.0 mL) and stirred for another 1 h. The deep amber solution was diluted with water (100 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 further purified by either prepatory HPLC or by recrystallization in hot ethanol or a mixture of hot ethanol and chloroform.

Workup

  1. stirringstirred for another 1 h
  2. customThe resulting precipitate was collected on a sintered funnel
  3. washwhile rinsing with water
  4. customThe crude product was further purified by either prepatory HPLC or by recrystallization in hot ethanol
  5. additiona mixture of hot ethanol and chloroform

Sources & evidence

ORD record
ord-548a333bd5f145bb921d387109d204aa
Source dataset
uspto-grants-2013_05
Patent number
US08436031B2

Reaction notes

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