3-Amino-4-methoxybenzanilide → HCID 53750396, compound

HRID 1859744Notes

Reaction equation

HRID 1859744 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[CH3:19][N:20]1[CH:24]=[C:23]([S:25](Cl)(=[O:27])=[O:26])[N:22]=[CH:21]1>N1C=CC=CC=1>[CH3:19][N:20]1[CH:24]=[C:23]([S:25]([NH:1][C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:6])(=[O:27])=[O:26])[N:22]=[CH:21]1

Participants

4

Reactant 2

HCID 84263-Amino-4-methoxybenzanilideHCID 27368871-methyl-1H-imidazole-4-sulfonyl chloride

Product 1

HCID 53750396HCID 53750396, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pyridine (25 mL) was added to a mixture of 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10 mmol) and 1-methylimidazole-4-sulfonyl chloride (1.82 g, 10 mmol) and the mixture agitated then allowed to stand at room temperature. After 4 days, the mixture was partitioned between ethyl acetate (400 mL) and water (400 mL). The insoluble material was collected by filtration, washed with water, and air dried. The organic extract was washed with water (2×400 mL), 1N HCl (100 mL), and brine (100 mL), then dried over magnesium sulfate, filtered, and stripped of solvent. The residue was combined with the solid obtained above to afford the product (3.07 g); m.p. 250-252° C., after trituration in hexanes/ethyl acetate (1:1).

Workup

  1. customto stand at room temperature
  2. customthe mixture was partitioned between ethyl acetate (400 mL) and water (400 mL)
  3. filtrationThe insoluble material was collected by filtration
  4. washwashed with water, and air
  5. customdried
  6. extractionThe organic extract
  7. washwas washed with water (2×400 mL), 1N HCl (100 mL), and brine (100 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customobtained above

Sources & evidence

ORD record
ord-bc2cd4c428534dbeb6523f5c27e024ac
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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