Water → HCID 28401654, compound

HRID 2358662Notes

Reaction equation

HRID 2358662 reaction equation
[Br: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:18])[CH3:17])=[CH:11][CH:10]=2)=[C:4]([N+:19]([O-])=O)[CH:3]=1.[Cl-].[NH4+].C1COCC1.O>CO.[Fe]>[NH2:19][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 9172357HCID 9172357, compound

Product 1

HCID 28401654HCID 28401654, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent2×

Procedure

A solution of the product of Example 106a (1.4 g, 3.9 mmol), iron powder (0.874 g, 15.6 mmol) and ammonium chloride (0.253 g, 4.68 mmol) in a methanol (6 mL), THF (6 mL), and water (2 mL) solution was heated to reflux for 1.5 hours. The resultant mixture was diluted with methanol (50 mL) and filtered through a pad of celite. The filtrate was concentrated under vacuum to a volume of 10 mL, the solution diluted with water (50 mL) and extracted with ethyl acetate. The combined extracts were washed with 10% sodium chloride then dried over magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (1.2 g, 92%).

Workup

  1. temperatureto reflux for 1.5 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated under vacuum to a volume of 10 mL
  4. additionthe solution diluted with water (50 mL)
  5. extractionextracted with ethyl acetate
  6. washThe combined extracts were washed with 10% sodium chloride
  7. dry with materialthen dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c628c2be9d464c3f97770f452ad93f29
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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