HCID 11485504, compound → HCID 11416854, compound

HRID 1787506Notes

Reaction equation

HRID 1787506 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10](=[O:26])[N:11]([CH2:24][CH3:25])[N:12]=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]=2[CH:15](O)[CH3:16])[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1.OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10](=[O:26])[N:11]([CH2:24][CH3:25])[N:12]=[C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:14]=2[CH:15]=[CH2:16])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 11485504HCID 11485504, compound

Product 1

HCID 11416854HCID 11416854, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 1140TolueneSolvent

Procedure

To a solution of the title compound of example 1 (185 mg, 0.5 mmol) in toluene (8 mL), H2SO4 adsorbed on silica gel (Chavetz et al., Synthetic Communications, 24, 2325, 1884) (400 mg) was added portionwise during 4 h at 80° C. Then silica gel was filtered off and the residue was thoroughly washed with acetone. Solvent was removed under reduced pressure and the residue was treated with ice water. The final product precipitated and was isolated by filtration (63% yield).

Workup

  1. additionwas added portionwise during 4 h at 80° C
  2. filtrationThen silica gel was filtered off
  3. washthe residue was thoroughly washed with acetone
  4. customSolvent was removed under reduced pressure
  5. additionthe residue was treated with ice water
  6. customThe final product precipitated
  7. customwas isolated by filtration (63% yield)

Sources & evidence

ORD record
ord-a287d7a32ab54dd68fcf030e26ed7db9
Source dataset
uspto-grants-2009_03
Patent number
US07511038B2

Reaction notes

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