Toluene → 2-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

HRID 2308320Notes

Reaction equation

HRID 2308320 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[Cl:26][C:27]1[CH:38]=[C:31]2[C:32](OC(=O)[NH:36][C:30]2=[CH:29][CH:28]=1)=[O:33]>O1CCCC1>[NH2:36][C:30]1[CH:29]=[CH:28][C:27]([Cl:26])=[CH:38][C:31]=1[C:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1)=[O:33]

Participants

6

Reactant 4

HCID 1140TolueneHCID 661742-Amino-5-chloropyridineHCID 784805-Chloroisatoic anhydrideHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-amino-5-chloropyridine (328 mg, 2.55 mmol) in tetrahydrofuran (5 ml) was 0.5M potassium bis(trimethylsilyl)amide in toluene (10 ml, 5.05 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (0.5 g, 2.55 mmol) at −78° C. The mixture was warmed up to r.t gradually and stirred overnight. After quenched by saturated ammonium chloride solution, the mixture was extracted by ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to give (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide (0.71 g. 100%). MS found for Cl2H9Cl2N3O M+=282, (M+2)+=284.

Workup

  1. customdropwise at −78° C
  2. temperatureThe mixture was warmed up
  3. stirringstirred overnight
  4. customAfter quenched by saturated ammonium chloride solution
  5. extractionthe mixture was extracted by ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-38f3804cc53f4014b6ff420cabf353aa
Source dataset
uspto-grants-2004_12
Patent number
US06835739B2

Reaction notes

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