Sodium Carbonate → HCID 86615560, compound

HRID 605221Notes

Reaction equation

HRID 605221 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:26])[C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)=[C:11]([N+:23]([O-])=O)[CH:10]=2)=[N:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.C(O)C.O.C(OCC)(=O)C.[Fe]>[NH2:23][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[S:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:8]([NH:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][N:4]=1)=[O:26]

Participants

8

Reactant 2

HCID 10340Sodium CarbonateHCID 86615559HCID 86615559, compound

Product 1

HCID 86615560HCID 86615560, compoundYield 90%

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the product of Example 202B (414 mg, 0.9153 mmol) and iron powder (204.5 mg, 3.66 mmol) in acetic acid (7 mL) and ethanol (7 mL) was heated at reflux under a nitrogen atmosphere for 1 hour. The reaction was cooled to room temperature, and the mixture was diluted with water (50 mL) and ethyl acetate (100 mL). The aqueous pH was adjusted to 5 with solid sodium carbonate, the layers were separated, and the organic phase washed with water (2×50 mL) and brine (50 mL). The organic extract was dried over sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as a yellow solid (315 mg, 90%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 1 hour
  3. customthe layers were separated
  4. washthe organic phase washed with water (2×50 mL) and brine (50 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-31b2fc44dd074c84afd3e97cd53a4a55
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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