Water → HCID 67041207, compound

HRID 884021Notes

Reaction equation

HRID 884021 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=2[N+:28]([O-])=O)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10].[NH4+].[Cl-].C1COCC1.O>CCO.[Fe]>[NH2:28][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:18]=1[S:17][C:4]1[CH:5]=[CH:6][C:7]([NH:8][C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:14])[Cl:15])=[O:10])=[C:2]([F:1])[CH:3]=1)[C:22]([O:24][CH3:25])=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67041134HCID 67041134, compound

Product 1

HCID 67041207HCID 67041207, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

The product of Example 96C (2.8 g, 5.6 mmol), Fe powder (1.6 g, 28 mmol) and NH4Cl (1.5 g, 28 mmol) in a mixture of EtOH (28 mL), THF (14 mL) and water (28 mL) was gently refluxed for 1 hour. The reaction mixture was cooled and filtered through celite pad. The filtrate was concentrated. The aqueous residue was partitioned between ethyl acetate and water, and adjusted to pH 8-9 with NaHCO3. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated. The oily residue was separated by column chromatography (SiO2, n-hexane/ethyl acetate=3/1) to give the title compound as pale yellow crystal (1.3 g, 48%).

Workup

  1. temperaturewas gently refluxed for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite pad
  4. concentrationThe filtrate was concentrated
  5. customThe aqueous residue was partitioned between ethyl acetate and water
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe oily residue was separated by column chromatography (SiO2, n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-23bb3059f47f4df3bc3ed7d230deeefb
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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