Isatoic Anhydride → HCID 86659811, compound

HRID 1846328Notes

Reaction equation

HRID 1846328 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:16][CH:15]=1>CN(C=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:16][CH:15]=1)=[O:4]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 20152308N-(4-aminophenyl)propane-2-sulfonamide

Product 1

HCID 86659811HCID 86659811, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

Isatoic anhydride (0.690 g, 4.20 mmol) was added to a solution of N-(4-aminophenyl)propane-2-sulfonamide (0.910 g, 4.20 mmol) in DMF (15 mL) and heated at 115° C. overnight. The mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluting with 6% MeOH in CH2Cl2. Further purification was effected by reverse phase chromatography, eluting with 10% to 90% CH3CN in H2O with 0.1% TFA. The desired fractions were collected, basified, and extracted with EtOAc to afford 2-amino-N-(4-(1-methylethylsulfonamido)phenyl)benzamide (0.325 g, 23%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by flash chromatography on silica gel
  3. washeluting with 6% MeOH in CH2Cl2
  4. customFurther purification
  5. washeluting with 10% to 90% CH3CN in H2O with 0.1% TFA
  6. customThe desired fractions were collected
  7. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-87ba3a1ee4f44a89b7261fcd463e0569
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…