HCID 67040688, compound → HCID 67040402, compound

HRID 605226Notes

Reaction equation

HRID 605226 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][C:10]=2[N+:24]([O-])=O)=[CH:4][CH:3]=1>CCO.CC(O)=O.[Fe]>[NH2:24][C:10]1[CH:11]=[C:12]([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:9]=1[S:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

Participants

5

Reactant 1

HCID 67040688HCID 67040688, compound

Product 1

HCID 67040402HCID 67040402, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of the product from Example 220b (0.67 g, 1.8 mmol) and Fe powder (0.31 g, 5.5 mmol) in a mixture of EtOH (6.7 mL) and HOAc (6.7 mL) was gradually heated to 80° C. and heated at 80° C. for 3 hours. The reaction mixture was evaporated. The residue was portioned between EtOAc and 10% NaHCO3 and then filtered (through celite). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound, which was purified by washing with i-Pr2O to give the desired compound as pale brown crystals (0.53 g, 86%).

Workup

  1. temperatureheated at 80° C. for 3 hours
  2. customThe reaction mixture was evaporated
  3. filtrationfiltered (through celite)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customgiving the crude title compound, which
  9. customwas purified
  10. washby washing with i-Pr2O

Sources & evidence

ORD record
ord-e5b6acd5d72e4c2996c8e5c3c377128b
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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